[ { "file_name": "acs.joc.2c00176 example 1.png", "reaction_template": { "reactants": [ "*C(=O)NN=CC(F)(F)F", "N#CN" ], "products": [ "*C(=O)N1NC(C(F)(F)F)N=C1N" ] }, "detailed_reactions": { "a": { "reactants": [ "O=C(NN=CC(F)(F)F)c1ccccc1", "N#CN" ], "products": [ "NC1=NC(C(F)(F)F)NN1C(=O)c1ccccc1" ] }, "b": { "reactants": [ "Cc1ccccc1C(=O)NN=CC(F)(F)F", "N#CN" ], "products": [ "Cc1ccccc1C(=O)N1NC(C(F)(F)F)N=C1N" ] }, "c": { "reactants": [ "Cc1cccc(C(=O)NN=CC(F)(F)F)c1", "N#CN" ], "products": [ "Cc1cccc(C(=O)N2NC(C(F)(F)F)N=C2N)c1" ] }, "d": { "reactants": [ "Cc1ccc(C(=O)NN=CC(F)(F)F)cc1", "N#CN" ], "products": [ "Cc1ccc(C(=O)N2NC(C(F)(F)F)N=C2N)cc1" ] }, "e": { "reactants": [ "COc1ccc(C(=O)NN=CC(F)(F)F)cc1", "N#CN" ], "products": [ "COc1ccc(C(=O)N2NC(C(F)(F)F)N=C2N)cc1" ] }, "f": { "reactants": [ "Cc1cc(C)cc(C(=O)NN=CC(F)(F)F)c1", "N#CN" ], "products": [ "Cc1cc(C)cc(C(=O)N2NC(C(F)(F)F)N=C2N)c1" ] }, "g": { "reactants": [ "COc1cc(OC)cc(C(=O)NN=CC(F)(F)F)c1", "N#CN" ], "products": [ "COc1cc(OC)cc(C(=O)N2NC(C(F)(F)F)N=C2N)c1" ] }, "h": { "reactants": [ "O=C(NN=CC(F)(F)F)c1ccc2c(c1)OCO2", "N#CN" ], "products": [ "[H]N1C(C(F)(F)F)N=C(N)N1C(=O)c1ccc2c(c1)OCO2" ] }, "i": { "reactants": [ "O=C(NN=CC(F)(F)F)c1ccc(F)cc1", "N#CN" ], "products": [ "NC1=NC(C(F)(F)F)NN1C(=O)c1ccc(F)cc1" ] }, "j": { "reactants": [ "O=C(NN=CC(F)(F)F)c1ccc(Cl)cc1", "N#CN" ], "products": [ "NC1=NC(C(F)(F)F)NN1C(=O)c1ccc(Cl)cc1" ] }, "k": { "reactants": [ "O=C(NN=CC(F)(F)F)c1ccc(Br)cc1", "N#CN" ], "products": [ "NC1=NC(C(F)(F)F)NN1C(=O)c1ccc(Br)cc1" ] }, "l": { "reactants": [ "FC(F)(F)c1ccc(C(=O)NN=CC(F)(F)F)cc1", "N#CN" ], "products": [ "*c1ccc(C(=O)N2NC(C(F)(F)F)N=C2N)cc1" ] }, "m": { "reactants": [ "[O-][N+](=O)c1ccc(C(=O)NN=CC(F)(F)F)cc1", "N#CN" ], "products": [ "*c1ccc(C(=O)N2NC(C(F)(F)F)N=C2N)cc1" ] }, "n": { "reactants": [ "COC(=O)c1ccc(C(=O)NN=CC(F)(F)F)cc1", "N#CN" ], "products": [ "*c1ccc(C(=O)N2NC(C(F)(F)F)N=C2N)cc1" ] }, "o": { "reactants": [ "O=C(NN=CC(F)(F)F)c1ccc2ccccc2c1", "N#CN" ], "products": [ "NC1=NC(C(F)(F)F)NN1C(=O)c1ccc2ccccc2c1" ] }, "p": { "reactants": [ "O=C(NN=CC(F)(F)F)c1ccco1", "N#CN" ], "products": [ "[H]N1C(C(F)(F)F)N=C(N)N1C(=O)c1ccco1" ] }, "q": { "reactants": [ "O=C(NN=CC(F)(F)F)c1cccs1", "N#CN" ], "products": [ "[H]N1C(C(F)(F)F)N=C(N)N1C(=O)c1cccs1" ] }, "r": { "reactants": [ "O=C(NN=CC(F)(F)F)c1cc2sccc2s1", "N#CN" ], "products": [ "[H]N1C(C(F)(F)F)N=C(N)N1C(=O)c1cc2sccc2s1" ] }, "s": { "reactants": [ "O=C(c1ncccc1)NN=CC(F)(F)F", "N#CN" ], "products": [ "[H]N1C(C(F)(F)F)N=C(N)N1C(=O)c1ccccn1" ] }, "t": { "reactants": [ "O=C(Cc1ccccc1)NN=CC(F)(F)F", "N#CN" ], "products": [ "NC1=NC(C(F)(F)F)NN1C(=O)Cc1ccccc1" ] }, "u": { "reactants": [ "CC(=O)NN=CC(F)(F)F", "N#CN" ], "products": [ "CC(=O)N1NC(C(F)(F)F)N=C1N" ] }, "v": { "reactants": [ "O=C(C1CCCCC1)NN=CC(F)(F)F", "N#CN" ], "products": [ "NC1=NC(C(F)(F)F)NN1C(=O)C1CCCCC1" ] }, "w": { "reactants": [ "O=C(C(C)C)NN=CC(F)(F)F", "N#CN" ], "products": [ "CC(C)C(=O)N1NC(C(F)(F)F)N=C1N" ] }, "x": { "reactants": [ "O=C(NN=CC(F)(F)F)CCCCCCCCCCC", "N#CN" ], "products": [ "CCCCCCCCCCCC(=O)N1NC(C(F)(F)F)N=C1N" ] } } }, { "file_name": "acs.joc.2c00176 example 2.png", "reaction_template": { "reactants": [ "*C(=O)N1NC(C(F)(F)F)N=C1N" ], "products": [ "*C(=O)n1nc(C(F)(F)F)nc1N" ] }, "detailed_reactions": { "a": { "reactants": [ "NC1=NC(C(F)(F)F)NN1C(=O)c1ccccc1" ], "products": [ "Nc1nc(C(F)(F)F)nn1C(=O)c1ccccc1" ] }, "b": { "reactants": [ "Cc1ccccc1C(=O)N1NC(C(F)(F)F)N=C1N" ], "products": [ "Cc1ccccc1C(=O)n1nc(C(F)(F)F)nc1N" ] }, "c": { "reactants": [ "Cc1cccc(C(=O)N2NC(C(F)(F)F)N=C2N)c1" ], "products": [ "Cc1cccc(C(=O)n2nc(C(F)(F)F)nc2N)c1" ] }, "d": { "reactants": [ "NC1=NC(C(F)(F)F)NN1C(=O)c1ccc(Cl)cc1" ], "products": [ "Nc1nc(C(F)(F)F)nn1C(=O)c1ccc(Cl)cc1" ] }, "e": { "reactants": [ "NC1=NC(C(F)(F)F)NN1C(=O)c1ccc2ccccc2c1" ], "products": [ "Nc1nc(C(F)(F)F)nn1C(=O)c1ccc2ccccc2c1" ] }, "f": { "reactants": [ "NC1=NC(C(F)(F)F)NN1C(=O)c1cccs1" ], "products": [ "Nc1nc(C(F)(F)F)nn1C(=O)c1cccs1" ] }, "g": { "reactants": [ "NC1=NC(C(F)(F)F)NN1C(=O)C(C)C" ], "products": [ "CC(C)C(=O)n1nc(C(F)(F)F)nc1N" ] }, "h": { "reactants": [ "CCCCCCCCCCCC(=O)N1NC(C(F)(F)F)N=C1N" ], "products": [ "CCCCCCCCCCCC(=O)n1nc(C(F)(F)F)nc1N" ] } } }, { "file_name": "acs.joc.3c00062 example 1.png", "reaction_template": { "reactants": [ "[3*]C(=O)C=S(C)(C)=O", "O=Nc1ccccc1", "C#Cc1ccccc1" ], "products": [ "[3*]C(=O)[C@@H]1[C@@H](C(=O)c2ccccc2)N1c1ccccc1" ] }, "detailed_reactions": { "aaa": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "O=Nc1ccccc1", "C#Cc1ccccc1" ], "products": [ "O=C(c1ccccc1)[C@@H]1[C@@H](C(=O)c2ccccc2)N1c1ccccc1" ] }, "baa": { "reactants": [ "Cc1ccccc1C(=O)C=S(C)(C)=O", "O=Nc1ccccc1", "C#Cc1ccccc1" ], "products": [ "Cc1ccccc1C(=O)[C@@H]1[C@@H](C(=O)c2ccccc2)N1c1ccccc1" ] }, "caa": { "reactants": [ "Cc1cccc(C(=O)C=S(C)(C)=O)c1", "O=Nc1ccccc1", "C#Cc1ccccc1" ], "products": [ "Cc1cccc(C(=O)[C@@H]2[C@@H](C(=O)c3ccccc3)N2c2ccccc2)c1" ] }, "daa": { "reactants": [ "Cc1ccc(C(=O)C=S(C)(C)=O)cc1", "O=Nc1ccccc1", "C#Cc1ccccc1" ], "products": [ "Cc1ccc(C(=O)[C@@H]2[C@@H](C(=O)c3ccccc3)N2c2ccccc2)cc1" ] }, "eaa": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccc(OC)cc1", "O=Nc1ccccc1", "C#Cc1ccccc1" ], "products": [ "COc1ccc(C(=O)[C@@H]2[C@@H](C(=O)c3ccccc3)N2c2ccccc2)cc1" ] }, "faa": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1F", "O=Nc1ccccc1", "C#Cc1ccccc1" ], "products": [ "O=C(c1ccccc1)[C@@H]1[C@@H](C(=O)c2ccccc2F)N1c1ccccc1" ] }, "gaa": { "reactants": [ "CS(C)(=O)=CC(=O)c1cccc(F)c1", "O=Nc1ccccc1", "C#Cc1ccccc1" ], "products": [ "O=C(c1ccccc1)[C@@H]1[C@@H](C(=O)c2cccc(F)c2)N1c1ccccc1" ] }, "haa": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccc(F)cc1", "O=Nc1ccccc1", "C#Cc1ccccc1" ], "products": [ "O=C(c1ccccc1)[C@@H]1[C@@H](C(=O)c2ccc(F)cc2)N1c1ccccc1" ] }, "iaa": { "reactants": [ "CS(C)(=O)=CC(=O)c1cccc2ccccc12", "O=Nc1ccccc1", "C#Cc1ccccc1" ], "products": [ "O=C(c1ccccc1)[C@@H]1[C@@H](C(=O)c2cccc3ccccc23)N1c1ccccc1" ] }, "jaa": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccc2ccccc2c1", "O=Nc1ccccc1", "C#Cc1ccccc1" ], "products": [ "O=C(c1ccccc1)[C@@H]1[C@@H](C(=O)c2ccc3ccccc3c2)N1c1ccccc1" ] }, "kaa": { "reactants": [ "CS(C)(=O)=CC(=O)c1cccs1", "O=Nc1ccccc1", "C#Cc1ccccc1" ], "products": [ "O=C(c1ccccc1)[C@@H]1[C@@H](C(=O)c2cccs2)N1c1ccccc1" ] }, "laa": { "reactants": [ "CC(C)C(=O)C=S(C)(C)=O", "O=Nc1ccccc1", "C#Cc1ccccc1" ], "products": [ "CC(C)C(=O)[C@@H]1[C@@H](C(=O)c2ccccc2)N1c1ccccc1" ] }, "maa": { "reactants": [ "CS(C)(=O)=CC(=O)C1CCCCC1", "O=Nc1ccccc1", "C#Cc1ccccc1" ], "products": [ "O=C(c1ccccc1)[C@@H]1[C@@H](C(=O)C2CCCCC2)N1c1ccccc1" ] } } }, { "file_name": "acs.joc.3c00062 example 2.png", "reaction_template": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "[4*]N=O", "C#Cc1ccccc1" ], "products": [ "[4*]N1[C@H](C(=O)c2ccccc2)[C@H]1C(=O)c1ccccc1" ] }, "detailed_reactions": { "aba": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "Cc1c(N=O)cccc1", "C#Cc1ccccc1" ], "products": [ "Cc1ccc(C(=O)[C@@H]2[C@@H](C(=O)c3ccccc3)N2c2ccccc2C)cc1" ] }, "aca": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "Cc1cc(N=O)ccc1", "C#Cc1ccccc1" ], "products": [ "Cc1cccc(N2[C@H](C(=O)c3ccccc3)[C@H]2C(=O)c2ccccc2)c1" ] }, "ada": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "Cc1ccc(N=O)cc1", "C#Cc1ccccc1" ], "products": [ "Cc1ccc(N2[C@H](C(=O)c3ccccc3)[C@H]2C(=O)c2ccccc2)cc1" ] }, "aea": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "COc1ccc(N=O)cc1", "C#Cc1ccccc1" ], "products": [ "COc1ccc(N2[C@H](C(=O)c3ccccc3)[C@H]2C(=O)c2ccccc2)cc1" ] }, "afa": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "O=Nc1ccccc1Cl", "C#Cc1ccccc1" ], "products": [ "O=C(c1ccccc1)[C@@H]1[C@@H](C(=O)c2ccccc2)N1c1ccccc1Cl" ] }, "aga": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "O=Nc1cccc(Cl)c1", "C#Cc1ccccc1" ], "products": [ "O=C(c1ccccc1)[C@@H]1[C@@H](C(=O)c2ccccc2)N1c1cccc(Cl)c1" ] }, "aha": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "Clc1ccc(N=O)cc1", "C#Cc1ccccc1" ], "products": [ "O=C(c1ccccc1)[C@@H]1[C@@H](C(=O)c2ccccc2)N1c1ccc(Cl)cc1" ] }, "aia": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "Fc1c(N=O)cccc1", "C#Cc1ccccc1" ], "products": [ "O=C(c1ccccc1)[C@@H]1[C@@H](C(=O)c2ccccc2)N1c1ccccc1F" ] }, "aja": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "O=Nc1cccc(F)c1", "C#Cc1ccccc1" ], "products": [ "O=C(c1ccccc1)[C@@H]1[C@@H](C(=O)c2ccccc2)N1c1cccc(F)c1" ] }, "aka": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "O=Nc1ccc(F)cc1", "C#Cc1ccccc1" ], "products": [ "O=C(c1ccccc1)[C@@H]1[C@@H](C(=O)c2ccccc2)N1c1ccc(F)cc1" ] }, "ala": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "Cc1cc(C)cc(N=O)c1", "C#Cc1ccccc1" ], "products": [ "Cc1cc(C)cc(N2[C@H](C(=O)c3ccccc3)[C@H]2C(=O)c2ccccc2)c1" ] }, "ama": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "O=Nc1ccncc1", "C#Cc1ccccc1" ], "products": [ "O=C(c1ccccc1)[C@@H]1[C@@H](C(=O)c2ccccc2)N1c1ccncc1" ] }, "ana": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "CC(=O)OC(C)(C)N=O", "C#Cc1ccccc1" ], "products": [ "CC(=O)OC(C)(C)N1[C@H](C(=O)c2ccccc2)[C@H]1C(=O)c1ccccc1" ] } } }, { "file_name": "acs.joc.3c00062 example 3.png", "reaction_template": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "O=Nc1ccccc1", "C#C[Rf]" ], "products": [ "O=C([Rf])[C@@H]1[C@@H](C(=O)c2ccccc2)N1c1ccccc1" ] }, "detailed_reactions": { "aab": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "O=Nc1ccccc1", "C#Cc1ccccc1C" ], "products": [ "Cc1ccccc1C(=O)[C@@H]1[C@@H](C(=O)c2ccccc2)N1c1ccccc1" ] }, "aac": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "O=Nc1ccccc1", "C#Cc1cccc(C)c1" ], "products": [ "Cc1cccc(C(=O)[C@@H]2[C@@H](C(=O)c3ccccc3)N2c2ccccc2)c1" ] }, "aad": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "O=Nc1ccccc1", "C#Cc1ccc(C)cc1" ], "products": [ "Cc1ccc(C(=O)[C@@H]2[C@@H](C(=O)c3ccccc3)N2c2ccccc2)cc1" ] }, "aae": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "O=Nc1ccccc1", "C#Cc1ccc(OC)cc1" ], "products": [ "COc1ccc(C(=O)[C@@H]2[C@@H](C(=O)c3ccccc3)N2c2ccccc2)cc1" ] }, "aaf": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "O=Nc1ccccc1", "C#Cc1ccccc1F" ], "products": [ "O=C(c1ccccc1)[C@@H]1[C@@H](C(=O)c2ccccc2F)N1c1ccccc1" ] }, "aag": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "O=Nc1ccccc1", "C#Cc1cccc(F)c1" ], "products": [ "O=C(c1ccccc1)[C@@H]1[C@@H](C(=O)c2cccc(F)c2)N1c1ccccc1" ] }, "aah": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "O=Nc1ccccc1", "C#Cc1ccc(F)cc1" ], "products": [ "O=C(c1ccccc1)[C@@H]1[C@@H](C(=O)c2ccc(F)cc2)N1c1ccccc1" ] }, "aai": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "O=Nc1ccccc1", "C#Cc1ccc(Cl)cc1" ], "products": [ "O=C(c1ccccc1)[C@@H]1[C@@H](C(=O)c2ccc(Cl)cc2)N1c1ccccc1" ] }, "aaj": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "O=Nc1ccccc1", "C#Cc1ccc([N+](=O)[O-])cc1" ], "products": [ "O=C(c1ccccc1)[C@@H]1[C@@H](C(=O)c2ccc([N+](=O)[O-])cc2)N1c1ccccc1" ] }, "aak": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "O=Nc1ccccc1", "C#Cc1ccsc1" ], "products": [ "O=C(c1ccccc1)[C@@H]1[C@@H](C(=O)c2ccsc2)N1c1ccccc1" ] }, "aal": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "O=Nc1ccccc1", "C#CCCCC" ], "products": [ "CCCCC(=O)[C@@H]1[C@@H](C(=O)c2ccccc2)N1c1ccccc1" ] }, "aam": { "reactants": [ "CS(C)(=O)=CC(=O)c1ccccc1", "O=Nc1ccccc1", "C#CCCl" ], "products": [ "O=C(CCl)[C@@H]1[C@@H](C(=O)c2ccccc2)N1c1ccccc1" ] } } }, { "file_name": "acs.joc.3c00760 example 1.png", "reaction_template": { "reactants": [ "C#Cc1ccccc1C(=O)O", "*" ], "products": [ "*C1(C)OC(=O)c2ccccc21" ] }, "detailed_reactions": { "a": { "reactants": [ "C#Cc1ccccc1C(=O)O", "Cc1cccc(C)c1O" ], "products": [ "Cc1cc(C2(C)OC(=O)c3ccccc32)cc(C)c1O" ] }, "b": { "reactants": [ "C#Cc1ccccc1C(=O)O", "COc1cc(O)cc(OC)c1" ], "products": [ "COc1cc(O)c(C2(C)OC(=O)c3ccccc32)c(OC)c1" ] }, "c": { "reactants": [ "C#Cc1ccccc1C(=O)O", "Oc1c(Br)cccc1Br" ], "products": [ "CC1(c2cc(Br)c(O)c(Br)c2)OC(=O)c2ccccc21" ] }, "d": { "reactants": [ "C#Cc1ccccc1C(=O)O", "Oc1cc(Br)cc(Br)c1" ], "products": [ "CC1(c2c(O)cc(Br)cc2Br)OC(=O)c2ccccc21" ] }, "e": { "reactants": [ "C#Cc1ccccc1C(=O)O", "Oc1cccc2ccccc12" ], "products": [ "CC1(c2ccc3ccccc3c2O)OC(=O)c2ccccc21" ] }, "f": { "reactants": [ "C#Cc1ccccc1C(=O)O", "Oc1ccc2ccccc2c1" ], "products": [ "CC1(c2c(O)ccc3ccccc23)OC(=O)c2ccccc21" ] }, "g": { "reactants": [ "C#Cc1ccccc1C(=O)O", "c1ccccc1" ], "products": [ "CC1(c2ccccc2)OC(=O)c2ccccc21" ] }, "h": { "reactants": [ "C#Cc1ccccc1C(=O)O", "Cc1ccccc1" ], "products": [ "Cc1ccc(C2(C)OC(=O)c3ccccc32)cc1" ] }, "ia": { "reactants": [ "C#Cc1ccccc1C(=O)O", "COc1ccccc1" ], "products": [ "COc1ccccc1C1(C)OC(=O)c2ccccc21" ] }, "ib": { "reactants": [ "C#Cc1ccccc1C(=O)O", "COc1ccccc1" ], "products": [ "COc1ccc(C2(C)OC(=O)c3ccccc32)cc1" ] }, "j": { "reactants": [ "C#Cc1ccccc1C(=O)O", "Cc1ccc(OC)cc1" ], "products": [ "COc1ccc(C)cc1C1(C)OC(=O)c2ccccc21" ] }, "k": { "reactants": [ "C#Cc1ccccc1C(=O)O", "CC(C)(C)Oc1ccccc1" ], "products": [ "CC(C)(C)Oc1ccc(C2(C)OC(=O)c3ccccc32)cc1" ] }, "l": { "reactants": [ "C#Cc1ccccc1C(=O)O", "c1cccs1" ], "products": [ "CC1(c2cccs2)OC(=O)c2ccccc21" ] }, "m": { "reactants": [ "C#Cc1ccccc1C(=O)O", "Cc1cccs1" ], "products": [ "Cc1ccc(C2(C)OC(=O)c3ccccc32)s1" ] }, "n": { "reactants": [ "C#Cc1ccccc1C(=O)O", "Cc1ccsc1" ], "products": [ "Cc1ccsc1C1(C)OC(=O)c2ccccc21" ] }, "o": { "reactants": [ "C#Cc1ccccc1C(=O)O", "Cn1cccc1" ], "products": [ "Cn1cccc1C1(C)OC(=O)c2ccccc21" ] }, "p": { "reactants": [ "C#Cc1ccccc1C(=O)O", "Cc1ccc[nH]1" ], "products": [ "Cc1ccc(C2(C)OC(=O)c3ccccc32)[nH]1" ] }, "q": { "reactants": [ "C#Cc1ccccc1C(=O)O", "Cc1ccco1" ], "products": [ "Cc1ccc(C2(C)OC(=O)c3ccccc32)o1" ] }, "r": { "reactants": [ "C#Cc1ccccc1C(=O)O", "Clc1ccccc1" ], "products": [ "CC1(c2ccccc2Cl)OC(=O)c2ccccc21" ] }, "s": { "reactants": [ "C#Cc1ccccc1C(=O)O", "O=[N+]([O-])c1ccccc1" ], "products": [ "CC1(c2ccccc2[N+](=O)[O-])OC(=O)c2ccccc21" ] } } }, { "file_name": "acs.joc.3c00760 example 2.png", "reaction_template": { "reactants": [ "C#Cc1ccccc1C(=O)O", "[1*]/C([2*])=C/[3*]" ], "products": [ "[1*]/C([2*])=C\\C1(C)OC(=O)c2ccccc21" ] }, "detailed_reactions": { "b": { "reactants": [ "C#Cc1ccccc1C(=O)O", "[3*]C=Cc1ccccc1" ], "products": [ "[H]/C(=C/C1(C)OC(=O)c2ccccc21)c1ccccc1" ] }, "c": { "reactants": [ "C#Cc1ccccc1C(=O)O", "[3*]C=C(C)c1ccccc1" ], "products": [ "CC(=CC1(C)OC(=O)c2ccccc21)c1ccccc1" ] }, "d": { "reactants": [ "C#Cc1ccccc1C(=O)O", "[3*]C=C(c1ccccc1)c1ccccc1" ], "products": [ "CC1(C=C(c2ccccc2)c2ccccc2)OC(=O)c2ccccc21" ] } } }, { "file_name": "acs.joc.3c00972 example 1.png", "reaction_template": { "reactants": [ "Brc1ccccc1", "[Cl-].[2*]OC(=O)[C@H]([7*])[NH3+]" ], "products": [ "[2*]OC(=O)[C@H]([7*])NC(=O)c1ccccc1" ] }, "detailed_reactions": { "a": { "reactants": [ "Brc1ccccc1", "CC(C)(C)OC(=O)[C@@H]([NH3+])Cc1ccccc1.[Cl-]" ], "products": [ "CC(C)(C)OC(=O)[C@H](Cc1ccccc1)NC(=O)c1ccccc1" ] }, "b": { "reactants": [ "Brc1ccccc1", "COC(=O)[C@H](C)[NH3+].[Cl-]" ], "products": [ "COC(=O)[C@H](C)NC(=O)c1ccccc1" ] }, "c": { "reactants": [ "Brc1ccccc1", "COC(=O)[C@@H]([NH3+])C(C)C.[Cl-]" ], "products": [ "COC(=O)[C@@H](NC(=O)c1ccccc1)C(C)C" ] }, "d": { "reactants": [ "Brc1ccccc1", "CC[C@H](C)[C@H]([NH3+])C(=O)OC.[Cl-]" ], "products": [ "CC[C@H](C)[C@H](NC(=O)c1ccccc1)C(=O)OC" ] }, "e": { "reactants": [ "Brc1ccccc1", "COC(=O)[C@@H]([NH3+])CC(C)C.[Cl-]" ], "products": [ "COC(=O)[C@H](CC(C)C)NC(=O)c1ccccc1" ] }, "f": { "reactants": [ "Brc1ccccc1", "CCOC(=O)[C@H]([NH3+])c1ccccc1.[Cl-]" ], "products": [ "CCOC(=O)[C@H](NC(=O)c1ccccc1)c1ccccc1" ] }, "g": { "reactants": [ "Brc1ccccc1", "COC(=O)[C@@H]([NH3+])Cc1ccc(OC(C)(C)C)cc1.[Cl-]" ], "products": [ "COC(=O)[C@H](Cc1ccc(OC(C)(C)C)cc1)NC(=O)c1ccccc1" ] }, "h": { "reactants": [ "Brc1ccccc1", "COC(=O)[C@@H]([NH3+])COC(C)(C)C.[Cl-]" ], "products": [ "COC(=O)[C@H](COC(C)(C)C)NC(=O)c1ccccc1" ] }, "i": { "reactants": [ "Brc1ccccc1", "COC(=O)[C@@H]([NH3+])[C@@H](C)OC(C)(C)C.[Cl-]" ], "products": [ "COC(=O)[C@@H](NC(=O)c1ccccc1)[C@@H](C)OC(C)(C)C" ] }, "j": { "reactants": [ "Brc1ccccc1", "COC(=O)[C@@H]([NH3+])CCC(=O)OC(C)(C)C.[Cl-]" ], "products": [ "COC(=O)[C@H](CCC(=O)OC(C)(C)C)NC(=O)c1ccccc1" ] }, "k": { "reactants": [ "Brc1ccccc1", "CC(C)(C)OC(=O)[C@@H]1CCC[NH2+]1.[Cl-]" ], "products": [ "CC(C)(C)OC(=O)[C@@H]1CCCN1C(=O)c1ccccc1" ] }, "l": { "reactants": [ "Brc1ccccc1", "COC(=O)[C@@H]([NH3+])CCCCNC(=O)OC(C)(C)C.[Cl-]" ], "products": [ "COC(=O)[C@H](CCCCNC(=O)OC(C)(C)C)NC(=O)c1ccccc1" ] } } }, { "file_name": "acs.joc.3c01171 example 1.png", "reaction_template": { "reactants": [ "[1*]C(=O)C1CC1C([H])=O", "[H]C(=O)C(C#Cc1ccccc1)=Cc1ccccc1" ], "products": [ "[1*]C(=O)CC[C@H]1C(=O)OC=C(C#Cc2ccccc2)[C@H]1c1ccccc1" ] }, "detailed_reactions": { "a": { "reactants": [ "O=CC1CC1C(=O)c1ccccc1", "O=CC(C#Cc1ccccc1)=Cc1ccccc1" ], "products": [ "O=C(CC[C@H]1C(=O)OC=C(C#Cc2ccccc2)[C@H]1c1ccccc1)c1ccccc1" ] }, "b": { "reactants": [ "COc1ccc(C(=O)C2CC2C=O)cc1", "O=CC(C#Cc1ccccc1)=Cc1ccccc1" ], "products": [ "COc1ccc(C(=O)CC[C@H]2C(=O)OC=C(C#Cc3ccccc3)[C@H]2c2ccccc2)cc1" ] }, "c": { "reactants": [ "Cc1ccc(C(=O)C2CC2C=O)cc1", "O=CC(C#Cc1ccccc1)=Cc1ccccc1" ], "products": [ "Cc1ccc(C(=O)CC[C@H]2C(=O)OC=C(C#Cc3ccccc3)[C@H]2c2ccccc2)cc1" ] }, "d": { "reactants": [ "O=CC1CC1C(=O)c1ccc(Br)cc1", "O=CC(C#Cc1ccccc1)=Cc1ccccc1" ], "products": [ "O=C(CC[C@H]1C(=O)OC=C(C#Cc2ccccc2)[C@H]1c1ccccc1)c1ccc(Br)cc1" ] }, "e": { "reactants": [ "O=CC1CC1C(=O)c1ccc(Cl)cc1", "O=CC(C#Cc1ccccc1)=Cc1ccccc1" ], "products": [ "O=C(CC[C@H]1C(=O)OC=C(C#Cc2ccccc2)[C@H]1c1ccccc1)c1ccc(Cl)cc1" ] }, "f": { "reactants": [ "O=CC1CC1C(=O)c1ccc(F)cc1", "O=CC(C#Cc1ccccc1)=Cc1ccccc1" ], "products": [ "O=C(CC[C@H]1C(=O)OC=C(C#Cc2ccccc2)[C@H]1c1ccccc1)c1ccc(F)cc1" ] }, "g": { "reactants": [ "O=CC1CC1C(=O)c1cccc(OC)c1", "O=CC(C#Cc1ccccc1)=Cc1ccccc1" ], "products": [ "COc1cccc(C(=O)CC[C@H]2C(=O)OC=C(C#Cc3ccccc3)[C@H]2c2ccccc2)c1" ] }, "h": { "reactants": [ "O=CC1CC1C(=O)c1cccc(Br)c1", "O=CC(C#Cc1ccccc1)=Cc1ccccc1" ], "products": [ "Cl.O=C(CC[C@H]1C(=O)OC=C(C#Cc2ccccc2)[C@H]1c1ccccc1)c1cccc(Br)c1" ] }, "i": { "reactants": [ "O=CC1CC1C(=O)c1cccc(Cl)c1", "O=CC(C#Cc1ccccc1)=Cc1ccccc1" ], "products": [ "O=C(CC[C@H]1C(=O)OC=C(C#Cc2ccccc2)[C@H]1c1ccccc1)c1cccc(Cl)c1" ] }, "j": { "reactants": [ "O=CC1CC1C(=O)c1ccccc1OC", "O=CC(C#Cc1ccccc1)=Cc1ccccc1" ], "products": [ "COc1ccccc1C(=O)CC[C@H]1C(=O)OC=C(C#Cc2ccccc2)[C@H]1c1ccccc1" ] }, "k": { "reactants": [ "O=CC1CC1C(=O)c1ccccc1Cl", "O=CC(C#Cc1ccccc1)=Cc1ccccc1" ], "products": [ "O=C(CC[C@H]1C(=O)OC=C(C#Cc2ccccc2)[C@H]1c1ccccc1)c1ccccc1Cl" ] }, "l": { "reactants": [ "O=CC1CC1C(=O)c1cccs1", "O=CC(C#Cc1ccccc1)=Cc1ccccc1" ], "products": [ "O=C(CC[C@H]1C(=O)OC=C(C#Cc2ccccc2)[C@H]1c1ccccc1)c1cccs1" ] } } }, { "file_name": "acs.joc.3c01171 example 2.png", "reaction_template": { "reactants": [ "[H]C(=O)C1CC1C(=O)c1ccccc1", "[2*]/C=C(\\C#C[3*])C([H])=O" ], "products": [ "[2*][C@@H]1C(C#C[3*])=COC(=O)[C@@H]1CCC(=O)c1ccccc1" ] }, "detailed_reactions": { "m": { "reactants": [ "O=CC1CC1C(=O)c1ccccc1", "Cc1ccc(C#CC(C=O)=Cc2ccccc2)cc1" ], "products": [ "Cc1ccc(C#CC2=COC(=O)[C@H](CCC(=O)c3ccccc3)[C@@H]2c2ccccc2)cc1" ] }, "n": { "reactants": [ "O=CC1CC1C(=O)c1ccccc1", "O=CC(C#Cc1ccc(Cl)cc1)=Cc1ccccc1" ], "products": [ "O=C(CC[C@H]1C(=O)OC=C(C#Cc2ccc(Cl)cc2)[C@H]1c1ccccc1)c1ccccc1" ] }, "o": { "reactants": [ "O=CC1CC1C(=O)c1ccccc1", "O=CC(C#Cc1cccc(OC)c1)=Cc1ccccc1" ], "products": [ "COc1cccc(C#CC2=COC(=O)[C@H](CCC(=O)c3ccccc3)[C@@H]2c2ccccc2)c1" ] }, "p": { "reactants": [ "O=CC1CC1C(=O)c1ccccc1", "O=CC(C#Cc1cccc(F)c1)=Cc1ccccc1" ], "products": [ "O=C(CC[C@H]1C(=O)OC=C(C#Cc2cccc(F)c2)[C@H]1c1ccccc1)c1ccccc1" ] }, "q": { "reactants": [ "O=CC1CC1C(=O)c1ccccc1", "O=CC(C#C)=Cc1ccccc1" ], "products": [ "C#CC1=COC(=O)[C@H](CCC(=O)c2ccccc2)[C@@H]1c1ccccc1" ] }, "r": { "reactants": [ "O=CC1CC1C(=O)c1ccccc1", "O=CC(C#Cc1cccs1)=Cc1ccccc1" ], "products": [ "O=C(CC[C@H]1C(=O)OC=C(C#Cc2cccs2)[C@H]1c1ccccc1)c1ccccc1" ] }, "s": { "reactants": [ "O=CC1CC1C(=O)c1ccccc1", "O=CC(C#CC1CC1)=Cc2ccccc2" ], "products": [ "O=C(CC[C@H]1C(=O)OC=C(C#CC2CC2)[C@H]1c1ccccc1)c1ccccc1" ] }, "t": { "reactants": [ "O=CC1CC1C(=O)c1ccccc1", "O=CC(C#Cc1ccccc1)=Cc1ccccc1Cl" ], "products": [ "*.O=C(CC[C@H]1C(=O)OC=C(C#Cc2ccccc2)[C@H]1c1ccccc1Cl)c1ccccc1" ] } } }, { "file_name": "acs.joc.3c01355 example 1.png", "reaction_template": { "reactants": [ "[1*]SCc1ccco1", "[2*]SS[2*]" ], "products": [ "[1*]SS[2*]" ] }, "detailed_reactions": { "a": { "reactants": [ "CSCc1ccco1", "COc1ccc(SSc2ccc(OC)cc2)cc1" ], "products": [ "COc1ccc(SSC)cc1" ] }, "b": { "reactants": [ "CCSCc1ccco1", "COc1ccc(SSc2ccc(OC)cc2)cc1" ], "products": [ "CCSSc1ccc(OC)cc1" ] }, "c": { "reactants": [ "CCCSCc1ccco1", "COc1ccc(SSc2ccc(OC)cc2)cc1" ], "products": [ "CCCSSc1ccc(OC)cc1" ] }, "d": { "reactants": [ "CCCCSCc1ccco1", "COc1ccc(SSc2ccc(OC)cc2)cc1" ], "products": [ "CCCCSSc1ccc(OC)cc1" ] }, "e": { "reactants": [ "CCCCCSCc1ccco1", "COc1ccc(SSc2ccc(OC)cc2)cc1" ], "products": [ "CCCCCSSc1ccc(OC)cc1" ] }, "f": { "reactants": [ "CC(C)SCc1ccco1", "COc1ccc(SSc2ccc(OC)cc2)cc1" ], "products": [ "COc1ccc(SSC(C)C)cc1" ] }, "g": { "reactants": [ "CCC(C)SCc1ccco1", "COc1ccc(SSc2ccc(OC)cc2)cc1" ], "products": [ "CCC(C)SSc1ccc(OC)cc1" ] }, "h": { "reactants": [ "c1ccccc1SCc1ccco1", "COc1ccc(SSc2ccc(OC)cc2)cc1" ], "products": [ "COc1ccc(SSCc2ccccc2)cc1" ] }, "i": { "reactants": [ "N#CCSCc1ccco1", "COc1ccc(SSc2ccc(OC)cc2)cc1" ], "products": [ "COc1ccc(SSCC#N)cc1" ] }, "j": { "reactants": [ "OC(=O)CSCc1ccco1", "COc1ccc(SSc2ccc(OC)cc2)cc1" ], "products": [ "COc1ccc(SSCC(=O)O)cc1" ] }, "k": { "reactants": [ "COC(=O)CSCc1ccco1", "COc1ccc(SSc2ccc(OC)cc2)cc1" ], "products": [ "COC(=O)CSSc1ccc(OC)cc1" ] }, "l": { "reactants": [ "C#CCSCc1ccco1", "COc1ccc(SSc2ccc(OC)cc2)cc1" ], "products": [ "C#CCSSc1ccc(OC)cc1" ] }, "m": { "reactants": [ "CSCc1ccco1", "COc1c(SSc2ccccc2OC)cccc1" ], "products": [ "COc1ccccc1SSC" ] }, "n": { "reactants": [ "CSCc1ccco1", "COc1cc(SSc2cccc(OC)c2)ccc1" ], "products": [ "COc1cccc(SSC)c1" ] }, "o": { "reactants": [ "CSCc1ccco1", "[O-][N+](=O)c1cc(SSc2cccc([N+](=O)[O-])c2)ccc1" ], "products": [ "CSSc1cccc([N+](=O)[O-])c1" ] }, "p": { "reactants": [ "CSCc1ccco1", "O=[N+]([O-])c1ccc(SSc2ccc([N+](=O)[O-])cc2)cc1" ], "products": [ "CSSc1ccc([N+](=O)[O-])cc1" ] }, "q": { "reactants": [ "CSCc1ccco1", "c1ccc(SSc2ccccn2)nc1" ], "products": [ "CSSc1ccccn1" ] }, "r": { "reactants": [ "CSCc1ccco1", "O=C(O)CCSSCCC(=O)O" ], "products": [ "CSSCCC(=O)O" ] }, "s": { "reactants": [ "COC(=O)SCc1ccco1", "CCSSCC" ], "products": [ "CCSSCC(=O)OC" ] }, "t": { "reactants": [ "COC(=O)SCc1ccco1", "CCCSSCCC" ], "products": [ "CCCSSCC(=O)OC" ] }, "u": { "reactants": [ "COC(=O)SCc1ccco1", "CCCCSSCCCC" ], "products": [ "CCCCSSCC(=O)OC" ] }, "v": { "reactants": [ "COC(=O)SCc1ccco1", "CC(C)SSC(C)C" ], "products": [ "COC(=O)CSSC(C)C" ] }, "w": { "reactants": [ "COC(=O)SCc1ccco1", "CC(C)(C)SSC(C)(C)C" ], "products": [ "COC(=O)CSSC(C)(C)C" ] }, "x": { "reactants": [ "COC(=O)SCc1ccco1", "C1CCC(SSC2CCCCC2)CC1" ], "products": [ "COC(=O)CSSC1CCCCC1" ] } } }, { "file_name": "acs.joc.3c00976 example 1.png", "reaction_template": { "reactants": [ "*C1(C=C)COC(=O)O1", "Cc1ccc2occ(C#N)c(=O)c2c1" ], "products": [ "*[C@@]1(C=C)COC=C1C#N" ] }, "detailed_reactions": { "a": { "reactants": [ "C=CC1(c2ccccc2)COC(=O)O1", "Cc1ccc2occ(C#N)c(=O)c2c1" ], "products": [ "C=C[C@]1(c2ccccc2)COC=C1C#N" ] }, "b": { "reactants": [ "C=CC1(c2ccccc2OC)COC(=O)O1", "Cc1ccc2occ(C#N)c(=O)c2c1" ], "products": [ "C=C[C@]1(c2ccccc2OC)COC=C1C#N" ] }, "c": { "reactants": [ "C=CC1(c2cccc(OC)c2)COC(=O)O1", "Cc1ccc2occ(C#N)c(=O)c2c1" ], "products": [ "C=C[C@]1(c2cccc(OC)c2)COC=C1C#N" ] }, "d": { "reactants": [ "C=CC1(c2ccc(OC)cc2)COC(=O)O1", "Cc1ccc2occ(C#N)c(=O)c2c1" ], "products": [ "C=C[C@]1(c2ccc(OC)cc2)COC=C1C#N" ] }, "e": { "reactants": [ "C=CC1(c2ccc(C)cc2)COC(=O)O1", "Cc1ccc2occ(C#N)c(=O)c2c1" ], "products": [ "C=C[C@]1(c2ccc(C)cc2)COC=C1C#N" ] }, "f": { "reactants": [ "C=CC1(c2ccc(F)cc2)COC(=O)O1", "Cc1ccc2occ(C#N)c(=O)c2c1" ], "products": [ "C=C[C@]1(c2ccc(F)cc2)COC=C1C#N" ] }, "g": { "reactants": [ "C=CC1(c2ccc(Cl)cc2)COC(=O)O1", "Cc1ccc2occ(C#N)c(=O)c2c1" ], "products": [ "C=C[C@]1(c2ccc(Cl)cc2)COC=C1C#N" ] }, "h": { "reactants": [ "C=CC1(c2ccc(Br)cc2)COC(=O)O1", "Cc1ccc2occ(C#N)c(=O)c2c1" ], "products": [ "C=C[C@]1(c2ccc(Br)cc2)COC=C1C#N" ] }, "i": { "reactants": [ "C=CC1(c2ccc(F)cc2F)COC(=O)O1", "Cc1ccc2occ(C#N)c(=O)c2c1" ], "products": [ "C=C[C@]1(c2ccc(F)cc2F)COC=C1C#N" ] }, "j": { "reactants": [ "C=CC1(c2ccc(Cl)c(Cl)c2)COC(=O)O1", "Cc1ccc2occ(C#N)c(=O)c2c1" ], "products": [ "C=C[C@]1(c2ccc(Cl)c(Cl)c2)COC=C1C#N" ] }, "k": { "reactants": [ "C=CC1(c2cccc3ccccc23)COC(=O)O1", "Cc1ccc2occ(C#N)c(=O)c2c1" ], "products": [ "C=C[C@]1(c2cccc3ccccc23)COC=C1C#N" ] }, "l": { "reactants": [ "C=CC1(c2ccc3ccccc3c2)COC(=O)O1", "Cc1ccc2occ(C#N)c(=O)c2c1" ], "products": [ "C=C[C@]1(c2ccc3ccccc3c2)COC=C1C#N" ] }, "m": { "reactants": [ "C=CC1(c2ccco2)COC(=O)O1", "Cc1ccc2occ(C#N)c(=O)c2c1" ], "products": [ "C=C[C@]1(c2ccco2)COC=C1C#N" ] }, "n": { "reactants": [ "C=CC1(c2cccs2)COC(=O)O1", "Cc1ccc2occ(C#N)c(=O)c2c1" ], "products": [ "C=C[C@]1(c2cccs2)COC=C1C#N" ] }, "o": { "reactants": [ "C=CC1(CCc2ccccc2)COC(=O)O1", "Cc1ccc2occ(C#N)c(=O)c2c1" ], "products": [ "C=C[C@]1(CCc2ccccc2)COC=C1C#N" ] }, "p": { "reactants": [ "C=CC1(CCCCCCCCCCC)COC(=O)O1", "Cc1ccc2occ(C#N)c(=O)c2c1" ], "products": [ "C=CC1(CCCCCCCCCCC)COC=C1C#N" ] } } }, { "file_name": "acs.joc.3c00766 example 1.png", "reaction_template": { "reactants": [ "O=c1[nH]c(-c2ccccc2[N+](=O)[O-])nc2ccccc12", "*C=O" ], "products": [ "*C1Nc2ccccc2-c2nc3ccccc3c(=O)n21" ] }, "detailed_reactions": { "a": { "reactants": [ "O=c1[nH]c(-c2ccccc2[N+](=O)[O-])nc2ccccc12", "O=Cc1ccccc1" ], "products": [ "O=c1c2ccccc2nc2n1C(c1ccccc1)Nc1ccccc1-2" ] }, "b": { "reactants": [ "O=c1[nH]c(-c2ccccc2[N+](=O)[O-])nc2ccccc12", "Cc1ccccc1C=O" ], "products": [ "Cc1ccccc1C1Nc2ccccc2-c2nc3ccccc3c(=O)n21" ] }, "c": { "reactants": [ "O=c1[nH]c(-c2ccccc2[N+](=O)[O-])nc2ccccc12", "COc1ccc(C=O)cc1" ], "products": [ "COc1ccc(C2Nc3ccccc3-c3nc4ccccc4c(=O)n32)cc1" ] }, "d": { "reactants": [ "O=c1[nH]c(-c2ccccc2[N+](=O)[O-])nc2ccccc12", "O=Cc1ccccc1F" ], "products": [ "O=c1c2ccccc2nc2n1C(c1ccccc1F)Nc1ccccc1-2" ] }, "e": { "reactants": [ "O=c1[nH]c(-c2ccccc2[N+](=O)[O-])nc2ccccc12", "O=Cc1cccc(Cl)c1" ], "products": [ "O=c1c2ccccc2nc2n1C(c1cccc(Cl)c1)Nc1ccccc1-2" ] }, "f": { "reactants": [ "O=c1[nH]c(-c2ccccc2[N+](=O)[O-])nc2ccccc12", "O=Cc1ccccc1Br" ], "products": [ "O=c1c2ccccc2nc2n1C(c1ccccc1Br)Nc1ccccc1-2" ] }, "g": { "reactants": [ "O=c1[nH]c(-c2ccccc2[N+](=O)[O-])nc2ccccc12", "O=Cc1ccc(F)cc1" ], "products": [ "O=c1c2ccccc2nc2n1C(c1ccc(F)cc1)Nc1ccccc1-2" ] }, "h": { "reactants": [ "O=c1[nH]c(-c2ccccc2[N+](=O)[O-])nc2ccccc12", "O=Cc1ccc(Cl)cc1" ], "products": [ "O=c1c2ccccc2nc2n1C(c1ccc(Cl)cc1)Nc1ccccc1-2" ] }, "i": { "reactants": [ "O=c1[nH]c(-c2ccccc2[N+](=O)[O-])nc2ccccc12", "O=Cc1ccc(Br)cc1" ], "products": [ "O=c1c2ccccc2nc2n1C(c1ccc(Br)cc1)Nc1ccccc1-2" ] }, "j": { "reactants": [ "O=c1[nH]c(-c2ccccc2[N+](=O)[O-])nc2ccccc12", "O=Cc1ccc2ccc3cccc4ccc1c2c34" ], "products": [ "O=c1c2ccccc2nc2n1C(c1ccc3ccc4cccc5ccc1c3c45)Nc1ccccc1-2" ] }, "k": { "reactants": [ "O=c1[nH]c(-c2ccccc2[N+](=O)[O-])nc2ccccc12", "O=Cc1c(c2ccccc2)cccc1" ], "products": [ "O=c1c2ccccc2nc2n1C(c1ccccc1-c1ccccc1)Nc1ccccc1-2" ] }, "l": { "reactants": [ "O=c1[nH]c(-c2ccccc2[N+](=O)[O-])nc2ccccc12", "COc1ccc(c2ccccc2C=O)cc1" ], "products": [ "COc1ccc(-c2ccccc2C2Nc3ccccc3-c3nc4ccccc4c(=O)n32)cc1" ] }, "m": { "reactants": [ "O=c1[nH]c(-c2ccccc2[N+](=O)[O-])nc2ccccc12", "Fc1ccc(c2ccccc2C=O)cc1" ], "products": [ "O=c1c2ccccc2nc2n1C(c1ccccc1-c1ccc(F)cc1)Nc1ccccc1-2" ] }, "n": { "reactants": [ "O=c1[nH]c(-c2ccccc2[N+](=O)[O-])nc2ccccc12", "O=Cc1ccccc1C#Cc1ccccc1" ], "products": [ "C.O=c1c2ccccc2nc2n1C(c1ccccc1C#Cc1ccccc1)Nc1ccccc1-2" ] }, "o": { "reactants": [ "O=c1[nH]c(-c2ccccc2[N+](=O)[O-])nc2ccccc12", "O=Cc1ccc2ccccc2n1" ], "products": [ "O=c1c2ccccc2nc2n1C(c1ccc3ccccc3n1)Nc1ccccc1-2" ] }, "p": { "reactants": [ "O=c1[nH]c(-c2ccccc2[N+](=O)[O-])nc2ccccc12", "O=Cc1cccnc1" ], "products": [ "O=c1c2ccccc2nc2n1C(c1cccnc1)Nc1ccccc1-2" ] }, "q": { "reactants": [ "O=c1[nH]c(-c2ccccc2[N+](=O)[O-])nc2ccccc12", "O=CCc1ccccc1" ], "products": [ "O=c1c2ccccc2nc2n1C(Cc1ccccc1)Nc1ccccc1-2" ] }, "r": { "reactants": [ "O=c1[nH]c(-c2ccccc2[N+](=O)[O-])nc2ccccc12", "CC=O" ], "products": [ "CC1Nc2ccccc2-c2nc3ccccc3c(=O)n21" ] }, "s": { "reactants": [ "O=c1[nH]c(-c2ccccc2[N+](=O)[O-])nc2ccccc12", "CCC=O" ], "products": [ "CCC1Nc2ccccc2-c2nc3ccccc3c(=O)n21" ] }, "t": { "reactants": [ "O=c1[nH]c(-c2ccccc2[N+](=O)[O-])nc2ccccc12", "CC(C)C=O" ], "products": [ "CC(C)C1Nc2ccccc2-c2nc3ccccc3c(=O)n21" ] } } }, { "file_name": "acs.joc.3c01427 example 1.png", "reaction_template": { "reactants": [ "*N/N=C(/*)Cl", "O=Nc1ccccc1" ], "products": [ "*C(=Nc1ccccc1)/N=[N+](/*)[O-]" ] }, "detailed_reactions": { "a": { "reactants": [ "ClC(=NNc1ccccc1)c1ccccc1", "O=Nc1ccccc1" ], "products": [ "[O-]/[N+](=N\\C(=Nc1ccccc1)c1ccccc1)c1ccccc1" ] }, "b": { "reactants": [ "Fc1ccc(C(Cl)=NNc2ccccc2)cc1", "O=Nc1ccccc1" ], "products": [ "*c1ccc(C(=Nc2ccccc2)/N=[N+](\\[O-])c2ccccc2)cc1" ] }, "c": { "reactants": [ "Clc1ccc(C(Cl)=NNc2ccccc2)cc1", "O=Nc1ccccc1" ], "products": [ "*c1ccc(C(=Nc2ccccc2)/N=[N+](\\[O-])c2ccccc2)cc1" ] }, "d": { "reactants": [ "Brc1ccc(C(Cl)=NNc2ccccc2)cc1", "O=Nc1ccccc1" ], "products": [ "*c1ccc(C(=Nc2ccccc2)/N=[N+](\\[O-])c2ccccc2)cc1" ] }, "e": { "reactants": [ "N#Cc1ccc(C(Cl)=NNc2ccccc2)cc1", "O=Nc1ccccc1" ], "products": [ "N#Cc1ccc(C(=Nc2ccccc2)/N=[N+](\\[O-])c2ccccc2)cc1" ] }, "f": { "reactants": [ "O=[N+]([O-])c1ccc(C(Cl)=NNc2ccccc2)cc1", "O=Nc1ccccc1" ], "products": [ "O=[N+]([O-])c1ccc(C(=Nc2ccccc2)/N=[N+](\\[O-])c2ccccc2)cc1" ] }, "g": { "reactants": [ "Cc1ccc(C(Cl)=NNc2ccccc2)cc1", "O=Nc1ccccc1" ], "products": [ "Cc1ccc(C(=Nc2ccccc2)/N=[N+](\\[O-])c2ccccc2)cc1" ] }, "h": { "reactants": [ "COc1ccc(C(Cl)=NNc2ccccc2)cc1", "O=Nc1ccccc1" ], "products": [ "COc1ccc(C(=Nc2ccccc2)/N=[N+](\\[O-])c2ccccc2)cc1" ] }, "i": { "reactants": [ "COc1ccccc1C(Cl)=NNc1ccccc1", "O=Nc1ccccc1" ], "products": [ "COc1ccccc1C(=Nc1ccccc1)/N=[N+](\\[O-])c1ccccc1" ] }, "j": { "reactants": [ "ClC(=NNc1ccccc1)c1cccc(Cl)c1", "O=Nc1ccccc1" ], "products": [ "[O-]/[N+](=N\\C(=Nc1ccccc1)c1cccc(Cl)c1)c1ccccc1" ] }, "k": { "reactants": [ "ClC(=NNc1ccccc1)c1ccco1", "O=Nc1ccccc1" ], "products": [ "C*1cccc1C(=Nc1ccccc1)/N=[N+](\\[O-])c1ccccc1" ] }, "l": { "reactants": [ "ClC(=NNc1ccccc1)c1cccs1", "O=Nc1ccccc1" ], "products": [ "C*1cccc1C(=Nc1ccccc1)/N=[N+](\\[O-])c1ccccc1" ] }, "m": { "reactants": [ "ClC(=NNc1ccccc1)c1ccc2ccccc2c1", "O=Nc1ccccc1" ], "products": [ "[O-]/[N+](=N\\C(=Nc1ccccc1)c1ccc2ccccc2c1)c1ccccc1" ] }, "n": { "reactants": [ "Cc1ccc(NN=C(Cl)c2ccccc2)cc1", "O=Nc1ccccc1" ], "products": [ "Cc1ccc(/[N+]([O-])=N/C(=Nc2ccccc2)c2ccccc2)cc1" ] }, "o": { "reactants": [ "ClC(C)=NNc1ccccc1", "O=Nc1ccccc1" ], "products": [ "CC(=Nc1ccccc1)/N=[N+](\\[O-])c1ccccc1" ] }, "p": { "reactants": [ "ClC(Cc1ccccc1)=NNc1ccccc1", "O=Nc1ccccc1" ], "products": [ "[O-]/[N+](=N\\C(Cc1ccccc1)=Nc1ccccc1)c1ccccc1" ] }, "q": { "reactants": [ "ClC(C(=O)C)=NNc1ccccc1", "O=Nc1ccccc1" ], "products": [ "CC(=O)C(=Nc1ccccc1)/N=[N+](\\[O-])c1ccccc1" ] } } }, { "file_name": "acs.joc.3c01427 example 2.png", "reaction_template": { "reactants": [ "Cl/C(=N\\Nc1ccccc1)c1ccccc1", "*N=O" ], "products": [ "*/N=C(\\N=[N+](/[O-])c1ccccc1)c1ccccc1" ] }, "detailed_reactions": { "r": { "reactants": [ "Cl/C(=N\\Nc1ccccc1)c1ccccc1", "Fc1ccc(N=O)cc1" ], "products": [ "*c1ccc(/N=C(\\N=[N+](/[O-])c2ccccc2)c2ccccc2)cc1" ] }, "s": { "reactants": [ "Cl/C(=N\\Nc1ccccc1)c1ccccc1", "Clc1ccc(N=O)cc1" ], "products": [ "*c1ccc(/N=C(\\N=[N+](/[O-])c2ccccc2)c2ccccc2)cc1" ] }, "t": { "reactants": [ "Cl/C(=N\\Nc1ccccc1)c1ccccc1", "Brc1ccc(N=O)cc1" ], "products": [ "*c1ccc(/N=C(\\N=[N+](/[O-])c2ccccc2)c2ccccc2)cc1" ] }, "u": { "reactants": [ "Cl/C(=N\\Nc1ccccc1)c1ccccc1", "O=Nc1cccc(Br)c1" ], "products": [ "[O-]/[N+](=N\\C(=N/c1cccc(Br)c1)c1ccccc1)c1ccccc1" ] }, "v": { "reactants": [ "Cl/C(=N\\Nc1ccccc1)c1ccccc1", "Cc1ccc(N=O)cc1" ], "products": [ "Cc1ccc(/N=C(\\N=[N+](/[O-])c2ccccc2)c2ccccc2)cc1" ] }, "w": { "reactants": [ "Cl/C(=N\\Nc1ccccc1)c1ccccc1", "COc1ccc(N=O)cc1" ], "products": [ "COc1ccc(/N=C(\\N=[N+](/[O-])c2ccccc2)c2ccccc2)cc1" ] }, "x": { "reactants": [ "Cl/C(=N\\Nc1ccccc1)c1ccccc1", "COC(=O)c1ccc(N=O)cc1" ], "products": [ "COC(=O)c1ccc(/N=C(\\N=[N+](/[O-])c2ccccc2)c2ccccc2)cc1" ] }, "y": { "reactants": [ "Cl/C(=N\\Nc1ccccc1)c1ccccc1", "CCOC(=O)c1ccc(N=O)cc1" ], "products": [ "CCOC(=O)c1ccc(/N=C(\\N=[N+](/[O-])c2ccccc2)c2ccccc2)cc1" ] } } }, { "file_name": "acs.joc.3c00999 example 1.png", "reaction_template": { "reactants": [ "*C(=O)NSc1ccc(C)cc1", "C1COCCN1" ], "products": [ "*C(=O)/N=S(\\c1ccc(C)cc1)N1CCOCC1" ] }, "detailed_reactions": { "b": { "reactants": [ "Cc1ccc(SNC(=O)C(C)C)cc1", "C1COCCN1" ], "products": [ "Cc1ccc(/S(=N\\C(=O)C(C)C)N2CCOCC2)cc1" ] }, "c": { "reactants": [ "Cc1ccc(SNC(=O)C23CC4CC(CC(C4)C2)C3)cc1", "C1COCCN1" ], "products": [ "Cc1ccc(/S(=N\\C(=O)C23CC4CC(CC(C4)C2)C3)N2CCOCC2)cc1" ] }, "d": { "reactants": [ "Cc1ccc(SNC(=O)Cc2cccc3ccccc23)cc1", "C1COCCN1" ], "products": [ "Cc1ccc(/S(=N\\C(=O)Cc2cccc3ccccc23)N2CCOCC2)cc1" ] }, "e": { "reactants": [ "Cc1ccc(SNC(=O)c2ccc3ccccc3c2)cc1", "C1COCCN1" ], "products": [ "Cc1ccc(/S(=N\\C(=O)c2ccc3ccccc3c2)N2CCOCC2)cc1" ] }, "f": { "reactants": [ "Cc1ccc(SNC(=O)c2ccccc2Cl)cc1", "C1COCCN1" ], "products": [ "Cc1ccc(/S(=N\\C(=O)c2ccccc2Cl)N2CCOCC2)cc1" ] }, "g": { "reactants": [ "Cc1ccc(SNC(=O)c2ccc(C)cc2)cc1", "C1COCCN1" ], "products": [ "Cc1ccc(C(=O)/N=S(\\c2ccc(C)cc2)N2CCOCC2)cc1" ] }, "h": { "reactants": [ "COc1ccc(C(=O)NSc2ccc(C)cc2)cc1", "C1COCCN1" ], "products": [ "COc1ccc(C(=O)/N=S(\\c2ccc(C)cc2)N2CCOCC2)cc1" ] }, "i": { "reactants": [ "Cc1ccc(SNC(=O)C=Cc2ccccc2)cc1", "C1COCCN1" ], "products": [ "Cc1ccc(/S(=N\\C(=O)C=Cc2ccccc2)N2CCOCC2)cc1" ] } } }, { "file_name": "acs.joc.2c02738 example 1.png", "reaction_template": { "reactants": [ "*C#Cc1ccccc1B(O)O", "Brc1cccc2nccn12" ], "products": [ "*C#Cc1ccccc1-c1cccc2nccn12" ] }, "detailed_reactions": { "a": { "reactants": [ "CC(C)(C)c1ccc(C#Cc2ccccc2B(O)O)cc1", "Brc1cccc2nccn12" ], "products": [ "CC(C)(C)c1ccc(C#Cc2ccccc2-c2cccc3nccn23)cc1" ] }, "b": { "reactants": [ "OB(O)c1ccccc1C#Cc1ccc(F)cc1", "Brc1cccc2nccn12" ], "products": [ "Fc1ccc(C#Cc2ccccc2-c2cccc3nccn23)cc1" ] }, "c": { "reactants": [ "OB(O)c1ccccc1C#Cc1ccccc1", "Brc1cccc2nccn12" ], "products": [ "C(#Cc1ccccc1-c1cccc2nccn12)c1ccccc1" ] }, "d": { "reactants": [ "COc1ccc(C#Cc2ccccc2B(O)O)cc1", "Brc1cccc2nccn12" ], "products": [ "COc1ccc(C#Cc2ccccc2-c2cccc3nccn23)cc1" ] }, "e": { "reactants": [ "Cc1ccc(C#Cc2ccccc2B(O)O)cc1", "Brc1cccc2nccn12" ], "products": [ "Cc1ccc(C#Cc2ccccc2-c2cccc3nccn23)cc1" ] }, "f": { "reactants": [ "CN(C)c1ccc(C#Cc2ccccc2B(O)O)cc1", "Brc1cccc2nccn12" ], "products": [ "CN(C)c1ccc(C#Cc2ccccc2-c2cccc3nccn23)cc1" ] }, "g": { "reactants": [ "OB(O)c1ccccc1C#Cc1ccc(C(F)(F)F)cc1", "Brc1cccc2nccn12" ], "products": [ "FC(F)(F)c1ccc(C#Cc2ccccc2-c2cccc3nccn23)cc1" ] }, "h": { "reactants": [ "Cc1cccc(C#Cc2ccccc2B(O)O)c1", "Brc1cccc2nccn12" ], "products": [ "Cc1cccc(C#Cc2ccccc2-c2cccc3nccn23)c1" ] }, "i": { "reactants": [ "OB(O)c1ccccc1C#Cc1ccccc1F", "Brc1cccc2nccn12" ], "products": [ "Fc1ccccc1C#Cc1ccccc1-c1cccc2nccn12" ] }, "j": { "reactants": [ "OB(O)c1ccccc1C#Cc1ccc(Cl)cc1", "Brc1cccc2nccn12" ], "products": [ "Clc1ccc(C#Cc2ccccc2-c2cccc3nccn23)cc1" ] }, "k": { "reactants": [ "OB(O)c1ccccc1C#Cc1ccccc1Cl", "Brc1cccc2nccn12" ], "products": [ "Clc1ccccc1C#Cc1ccccc1-c1cccc2nccn12" ] } } }, { "file_name": "acs.joc.2c02738 example 2.png", "reaction_template": { "reactants": [ "*C#Cc1ccccc1-c1cccc2nccn12" ], "products": [ "*c1cc2ccccc2c2c1ccc1nccn12" ] }, "detailed_reactions": { "a": { "reactants": [ "CC(C)(C)c1ccc(C#Cc2ccccc2-c2cccc3nccn23)cc1" ], "products": [ "CC(C)(C)c1ccc(-c2cc3ccccc3c3c2ccc2nccn23)cc1" ] }, "b": { "reactants": [ "Fc1ccc(C#Cc2ccccc2-c2cccc3nccn23)cc1" ], "products": [ "Fc1ccc(-c2cc3ccccc3c3c2ccc2nccn23)cc1" ] }, "c": { "reactants": [ "C(#Cc1ccccc1-c1cccc2nccn12)c1ccccc1" ], "products": [ "c1ccc(-c2cc3ccccc3c3c2ccc2nccn23)cc1" ] }, "d": { "reactants": [ "COc1ccc(C#Cc2ccccc2-c2cccc3nccn23)cc1" ], "products": [ "COc1ccc(-c2cc3ccccc3c3c2ccc2nccn23)cc1" ] }, "e": { "reactants": [ "Cc1ccc(C#Cc2ccccc2-c2cccc3nccn23)cc1" ], "products": [ "Cc1ccc(-c2cc3ccccc3c3c2ccc2nccn23)cc1" ] }, "f": { "reactants": [ "CN(C)c1ccc(C#Cc2ccccc2-c2cccc3nccn23)cc1" ], "products": [ "CN(C)c1ccc(-c2cc3ccccc3c3c2ccc2nccn23)cc1" ] }, "g": { "reactants": [ "FC(F)(F)c1ccc(C#Cc2ccccc2-c2cccc3nccn23)cc1" ], "products": [ "FC(F)(F)c1ccc(-c2cc3ccccc3c3c2ccc2nccn23)cc1" ] }, "h": { "reactants": [ "Cc1cc(C#Cc2ccccc2-c2cccc3nccn23)ccc1" ], "products": [ "Cc1cc(-c2cc3ccccc3c3c2ccc2nccn23)ccc1" ] }, "i": { "reactants": [ "Fc1ccccc1C#Cc1ccccc1-c1cccc2nccn12" ], "products": [ "Fc1ccccc1-c1cc2ccccc2c2c1ccc1nccn12" ] }, "j": { "reactants": [ "Clc1ccc(C#Cc2ccccc2-c2cccc3nccn23)cc1" ], "products": [ "Clc1ccc(-c2cc3ccccc3c3c2ccc2nccn23)cc1" ] }, "k": { "reactants": [ "Clc1ccccc1C#Cc1ccccc1-c1cccc2nccn12" ], "products": [ "Clc1ccccc1-c1cc2ccccc2c2c1ccc1nccn12" ] } } }, { "file_name": "acs.joc.2c02738 example 3.png", "reaction_template": { "reactants": [ "*C#Cc1ccccc1-c1cccc2nccn12" ], "products": [ "*C1=Cc2ccccc2-c2cccc3ncc1n23" ] }, "detailed_reactions": { "10a": { "reactants": [ "C(C)(C)(C)c1ccc(C#Cc2ccccc2-c2cccc3nccn23)cc1" ], "products": [ "C(C)(C)(C)c1ccc(C2=Cc3ccccc3-c3cccc4ncc2n34)cc1" ] }, "10b": { "reactants": [ "Fc1ccc(C#Cc2ccccc2-c2cccc3nccn23)cc1" ], "products": [ "Fc1ccc(C2=Cc3ccccc3-c3cccc4ncc2n34)cc1" ] }, "10c": { "reactants": [ "C(#Cc1ccccc1-c1cccc2nccn12)c1ccccc1" ], "products": [ "C1=C(c2ccccc2)c2cnc3cccc(n23)-c2ccccc21" ] }, "10d": { "reactants": [ "COc1ccc(C#Cc2ccccc2-c2cccc3nccn23)cc1" ], "products": [ "COc1ccc(C2=Cc3ccccc3-c3cccc4ncc2n34)cc1" ] }, "10e": { "reactants": [ "Cc1ccc(C#Cc2ccccc2-c2cccc3nccn23)cc1" ], "products": [ "Cc1ccc(C2=Cc3ccccc3-c3cccc4ncc2n34)cc1" ] }, "10f": { "reactants": [ "CN(C)c1ccc(C#Cc2ccccc2-c2cccc3nccn23)cc1" ], "products": [ "CN(C)c1ccc(C2=Cc3ccccc3-c3cccc4ncc2n34)cc1" ] }, "10g": { "reactants": [ "FC(F)(F)c1ccc(C#Cc2ccccc2-c2cccc3nccn23)cc1" ], "products": [ "FC(F)(F)c1ccc(C2=Cc3ccccc3-c3cccc4ncc2n34)cc1" ] }, "10h": { "reactants": [ "Cc1cccc(C#Cc2ccccc2-c2cccc3nccn23)c1" ], "products": [ "Cc1cccc(C2=Cc3ccccc3-c3cccc4ncc2n34)c1" ] }, "10i": { "reactants": [ "Fc1ccccc1C#Cc1ccccc1-c1cccc2nccn12" ], "products": [ "Fc1ccccc1C1=Cc2ccccc2-c2cccc3ncc1n23" ] }, "10j": { "reactants": [ "Clc1ccc(C#Cc2ccccc2-c2cccc3nccn23)cc1" ], "products": [ "Clc1ccc(C2=Cc3ccccc3-c3cccc4ncc2n34)cc1" ] }, "10k": { "reactants": [ "Clc1ccccc1C#Cc1ccccc1-c1cccc2nccn12" ], "products": [ "Clc1ccccc1C1=Cc2ccccc2-c2cccc3ncc1n23" ] } } }, { "file_name": "acs.joc.3c00067 example 1.png", "reaction_template": { "reactants": [ "*C#CC(=O)OC", "C#CCN" ], "products": [ "*c1ncccc1C(=O)OC" ] }, "detailed_reactions": { "a": { "reactants": [ "COC(=O)C#Cc1ccccc1", "C#CCN" ], "products": [ "COC(=O)c1cccnc1-c1ccccc1" ] }, "b": { "reactants": [ "COC(=O)C#Cc1ccc(C)cc1", "C#CCN" ], "products": [ "COC(=O)c1cccnc1-c1ccc(C)cc1" ] }, "c": { "reactants": [ "COC(=O)C#Cc1ccc(OC)cc1", "C#CCN" ], "products": [ "COC(=O)c1cccnc1-c1ccc(OC)cc1" ] }, "d": { "reactants": [ "COC(=O)C#Cc1ccc(C(C)(C)C)cc1", "C#CCN" ], "products": [ "COC(=O)c1cccnc1-c1ccc(C(C)(C)C)cc1" ] }, "e": { "reactants": [ "COC(=O)C#Cc1ccccc1C", "C#CCN" ], "products": [ "COC(=O)c1cccnc1-c1ccccc1C" ] }, "f": { "reactants": [ "COC(=O)C#Cc1ccc(F)cc1", "C#CCN" ], "products": [ "COC(=O)c1cccnc1-c1ccc(F)cc1" ] }, "g": { "reactants": [ "COC(=O)C#Cc1ccc(Cl)cc1", "C#CCN" ], "products": [ "COC(=O)c1cccnc1-c1ccc(Cl)cc1" ] }, "h": { "reactants": [ "COC(=O)C#Cc1ccc(C#N)cc1", "C#CCN" ], "products": [ "COC(=O)c1cccnc1-c1ccc(C#N)cc1" ] }, "i": { "reactants": [ "COC(=O)C#Cc1ccc([N+](=O)[O-])cc1", "C#CCN" ], "products": [ "COC(=O)c1cccnc1-c1ccc([N+](=O)[O-])cc1" ] }, "j": { "reactants": [ "COC(=O)C#Cc1ccc(C(F)(F)F)cc1", "C#CCN" ], "products": [ "COC(=O)c1cccnc1-c1ccc(C(F)(F)F)cc1" ] }, "k": { "reactants": [ "COC(=O)C#Cc1cccc(Cl)c1", "C#CCN" ], "products": [ "COC(=O)c1cccnc1-c1cccc(Cl)c1" ] }, "l": { "reactants": [ "COC(=O)C#Cc1cccc([N+](=O)[O-])c1", "C#CCN" ], "products": [ "COC(=O)c1cccnc1-c1cccc([N+](=O)[O-])c1" ] }, "m": { "reactants": [ "CCCCC#CC(=O)OC", "C#CCN" ], "products": [ "CCCCc1ncccc1C(=O)OC" ] }, "n": { "reactants": [ "COC(=O)C#CC(=O)OC", "C#CCN" ], "products": [ "COC(OC)c1cccnc1-c1ccc(-c2ncccc2C(OC)OC)cc1" ] }, "o": { "reactants": [ "COC(=O)C#CC(=O)OC", "C#CCN" ], "products": [ "COC(=O)c1cccnc1C(=O)OC" ] } } }, { "file_name": "acs.joc.3c00534 example 1.png", "reaction_template": { "reactants": [ "[3*]C(=NNS(=O)(=O)c1ccc(C)cc1)c1ccccc1NC(=O)c1ccccc1" ], "products": [ "[3*]C1OC(c2ccccc2)=Nc2ccccc21" ] }, "detailed_reactions": { "aa": { "reactants": [ "Cc1ccc(S(=O)(=O)NN=C(c2ccc(C(C)(C)C)cc2)c2ccccc2NC(=O)c2ccccc2)cc1" ], "products": [ "CC(C)(C)c1ccc(C2OC(c3ccccc3)=Nc3ccccc32)cc1" ] }, "ab": { "reactants": [ "CC(=NNS(=O)(=O)c1ccc(C)cc1)c1ccccc1NC(=O)c1ccccc1" ], "products": [ "CC1OC(c2ccccc2)=Nc2ccccc21" ] }, "t": { "reactants": [ "Brc1ccc(C(=NNS(=O)(=O)c2ccc(C)cc2)c2ccccc2NC(=O)c2ccccc2)cc1" ], "products": [ "Brc1ccc(C2OC(c3ccccc3)=Nc3ccccc32)cc1" ] }, "u": { "reactants": [ "Clc1ccc(C(=NNS(=O)(=O)c2ccc(C)cc2)c2ccccc2NC(=O)c2ccccc2)cc1" ], "products": [ "Clc1ccc(C2OC(c3ccccc3)=Nc3ccccc32)cc1" ] }, "v": { "reactants": [ "Fc1ccc(C(=NNS(=O)(=O)c2ccc(C)cc2)c2ccccc2NC(=O)c2ccccc2)cc1" ], "products": [ "Fc1ccc(C2OC(c3ccccc3)=Nc3ccccc32)cc1" ] }, "w": { "reactants": [ "Cc1ccc(C(=NNS(=O)(=O)c2ccc(C)cc2)c2ccccc2NC(=O)c2ccccc2)cc1" ], "products": [ "Cc1ccc(C2OC(c3ccccc3)=Nc3ccccc32)cc1" ] }, "x": { "reactants": [ "COc1ccccc1C(=NNS(=O)(=O)c1ccc(C)cc1)c1ccccc1NC(=O)c1ccccc1" ], "products": [ "COc1ccccc1C1OC(c2ccccc2)=Nc2ccccc21" ] }, "y": { "reactants": [ "COc1cccc(C(=NNS(=O)(=O)c2ccc(C)cc2)c2ccccc2NC(=O)c2ccccc2)c1" ], "products": [ "COc1cccc(C2OC(c3ccccc3)=Nc3ccccc32)c1" ] }, "z": { "reactants": [ "COc1ccc(C(=NNS(=O)(=O)c2ccc(C)cc2)c2ccccc2NC(=O)c2ccccc2)cc1" ], "products": [ "COc1ccc(C2OC(c3ccccc3)=Nc3ccccc32)cc1" ] } } }, { "file_name": "acs.orglett.3c01437 example 1.png", "reaction_template": { "reactants": [ "*N/N=C(\\Br)C(F)(F)F", "OC1CSC(O)CS1" ], "products": [ "*n1ccc(C(F)(F)F)n1" ] }, "detailed_reactions": { "a": { "reactants": [ "Cc1ccc(N/N=C(\\Br)C(F)(F)F)cc1", "OC1CSC(O)CS1" ], "products": [ "Cc1ccc(-n2ccc(C(F)(F)F)n2)cc1" ] }, "b": { "reactants": [ "c1ccccc1COc1ccc(N/N=C(\\Br)C(F)(F)F)cc1", "OC1CSC(O)CS1" ], "products": [ "c1ccccc1COc1ccc(-n2ccc(C(F)(F)F)n2)cc1" ] }, "c": { "reactants": [ "COc1ccc(N/N=C(\\Br)C(F)(F)F)cc1", "OC1CSC(O)CS1" ], "products": [ "COc1ccc(-n2ccc(C(F)(F)F)n2)cc1" ] }, "d": { "reactants": [ "FC(F)(F)/C(Br)=N/Nc1ccccc1", "OC1CSC(O)CS1" ], "products": [ "FC(F)(F)c1ccn(-c2ccccc2)n1" ] }, "e": { "reactants": [ "CC(C)c1ccc(N/N=C(\\Br)C(F)(F)F)cc1", "OC1CSC(O)CS1" ], "products": [ "CC(C)c1ccc(-n2ccc(C(F)(F)F)n2)cc1" ] }, "f": { "reactants": [ "FC(F)(F)/C(Br)=N/Nc1ccc(Br)cc1", "OC1CSC(O)CS1" ], "products": [ "FC(F)(F)c1ccn(-c2ccc(Br)cc2)n1" ] }, "g": { "reactants": [ "FC(F)(F)/C(Br)=N/Nc1ccc(Cl)cc1", "OC1CSC(O)CS1" ], "products": [ "FC(F)(F)c1ccn(-c2ccc(Cl)cc2)n1" ] }, "h": { "reactants": [ "Fc1ccc(N/N=C(\\Br)C(F)(F)F)cc1", "OC1CSC(O)CS1" ], "products": [ "Fc1ccc(-n2ccc(C(F)(F)F)n2)cc1" ] }, "i": { "reactants": [ "FC(F)(F)/C(Br)=N/Nc1ccc(Cl)cc1Cl", "OC1CSC(O)CS1" ], "products": [ "FC(F)(F)c1ccn(-c2ccc(Cl)cc2Cl)n1" ] }, "j": { "reactants": [ "O=C(Oc1ccc(N/N=C(\\Br)C(F)(F)F)cc1)c1ccccc1", "OC1CSC(O)CS1" ], "products": [ "O=C(Oc1ccc(-n2ccc(C(F)(F)F)n2)cc1)c1ccccc1" ] }, "k": { "reactants": [ "FC(F)(F)/C(Br)=N/Nc1ccc(C(F)(F)F)cc1", "OC1CSC(O)CS1" ], "products": [ "FC(F)(F)c1ccc(-n2ccc(C(F)(F)F)n2)cc1" ] }, "l": { "reactants": [ "COC(=O)c1ccc(N/N=C(\\Br)C(F)(F)F)cc1", "OC1CSC(O)CS1" ], "products": [ "COC(=O)c1ccc(-n2ccc(C(F)(F)F)n2)cc1" ] }, "m": { "reactants": [ "FC(F)(F)/C(Br)=N/Nc1ccc(S(=O)(=O)N)cc1", "OC1CSC(O)CS1" ], "products": [ "FC(F)(F)c1ccn(-c2ccc(S(=O)(=O)N)cc2)n1" ] }, "n": { "reactants": [ "N#Cc1ccc(N/N=C(\\Br)C(F)(F)F)cc1", "OC1CSC(O)CS1" ], "products": [ "N#Cc1ccc(-n2ccc(C(F)(F)F)n2)cc1" ] }, "o": { "reactants": [ "O=[N+]([O-])c1ccc(N/N=C(\\Br)C(F)(F)F)cc1", "OC1CSC(O)CS1" ], "products": [ "O=[N+]([O-])c1ccc(-n2ccc(C(F)(F)F)n2)cc1" ] }, "p": { "reactants": [ "O=[N+]([O-])c1cccc(N/N=C(\\Br)C(F)(F)F)c1", "OC1CSC(O)CS1" ], "products": [ "O=[N+]([O-])c1cccc(-n2ccc(C(F)(F)F)n2)c1" ] } } }, { "file_name": "acs.orglett.3c01437 example 2.png", "reaction_template": { "reactants": [ "*N/N=C(/*)Cl", "OC1CSC(O)CS1" ], "products": [ "*c1ccn(*)n1" ] }, "detailed_reactions": { "q": { "reactants": [ "ClC(=NNc1ccccc1)c1ccccc1", "OC1CSC(O)CS1" ], "products": [ "c1ccc(-c2ccn(-c3ccccc3)n2)cc1" ] }, "r": { "reactants": [ "CCOC(=O)C(Cl)=NNc1ccc(C)cc1", "OC1CSC(O)CS1" ], "products": [ "CCOC(=O)c1ccn(-c2ccc(C)cc2)n1" ] }, "s": { "reactants": [ "CCOC(=O)C(Cl)=NNc1ccc(OC)cc1", "OC1CSC(O)CS1" ], "products": [ "CCOC(=O)c1ccn(-c2ccc(OC)cc2)n1" ] }, "t": { "reactants": [ "CC(=O)C(Cl)=NNc1ccc(C)cc1", "OC1CSC(O)CS1" ], "products": [ "CC(=O)c1ccn(-c2ccc(C)cc2)n1" ] }, "u": { "reactants": [ "COc1ccc(NN=C(Cl)C(C)=O)cc1", "OC1CSC(O)CS1" ], "products": [ "COc1ccc(-n2ccc(C(C)=O)n2)cc1" ] }, "v": { "reactants": [ "CC(=O)C(Cl)=NNc1ccc(Cl)cc1", "OC1CSC(O)CS1" ], "products": [ "CC(=O)c1ccn(-c2ccc(Cl)cc2)n1" ] }, "w": { "reactants": [ "CC(=O)C(Cl)=NNc1ccc(C(=O)OCC)cc1", "OC1CSC(O)CS1" ], "products": [ "CC(=O)c1ccn(-c2ccc(C(=O)OCC)cc2)n1" ] }, "x": { "reactants": [ "CC(=O)C(Cl)=NNc1ccc([N+](=O)[O-])cc1", "OC1CSC(O)CS1" ], "products": [ "CC(=O)c1ccn(-c2ccc([N+](=O)[O-])cc2)n1" ] }, "y": { "reactants": [ "CC(=O)C(Cl)=NNc1c(C)cc(C)cc1C", "OC1CSC(O)CS1" ], "products": [ "CC(=O)c1ccn(-c2c(C)cc(C)cc2C)n1" ] } } }, { "file_name": "acs.orglett.2c03811 example 1.png", "reaction_template": { "reactants": [ "[1*]C#CN([2*])[3*]" ], "products": [ "[2*]N([3*])c1nc(C)oc1[7*]" ] }, "detailed_reactions": { "a": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C)C#Cc2ccccc2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N(C)c2nc(C)oc2-c2ccccc2)cc1" ] }, "b": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C#Cc2ccccc2)Cc2ccccc2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N(Cc2ccccc2)c2nc(C)oc2-c2ccccc2)cc1" ] }, "c": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C#Cc2ccccc2)c2ccccc2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N(c2ccccc2)c2nc(C)oc2-c2ccccc2)cc1" ] }, "d": { "reactants": [ "CN(C#Cc1ccccc1)S(C)(=O)=O" ], "products": [ "Cc1nc(N(C)S(C)(=O)=O)c(-c2ccccc2)o1" ] }, "e": { "reactants": [ "CN(C#Cc1ccccc1)S(c2c([N+](=O)[O-])cccc2)(=O)=O" ], "products": [ "Cc1nc(N(C)S(c3c([N+](=O)[O-])cccc3)(=O)=O)c(-c2ccccc2)o1" ] }, "f": { "reactants": [ "c1ccccc1C#CN2CCOC2=O" ], "products": [ "Cc1nc(N2CCOC2=O)c(-c2ccccc2)o1" ] }, "g": { "reactants": [ "O=S(=O)(c1ccccc1)N(C#Cc1ccccc1)S(=O)(=O)c1ccccc1" ], "products": [ "Cc1nc(N(S(=O)(=O)c2ccccc2)S(=O)(=O)c2ccccc2)c(-c2ccccc2)o1" ] }, "h": { "reactants": [ "c3cccc1c3c2ccccc2n1-C#Cc1ccccc1" ], "products": [ "c3cccc1c3c2ccccc2n1-c1nc(C)oc1-c1ccccc1" ] }, "i": { "reactants": [ "CCOC(=O)c1cc2ccccc2n1-C#Cc1ccccc1" ], "products": [ "CCOC(=O)c1cc2ccccc2n1-c1nc(C)oc1-c1ccccc1" ] }, "j": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C)C#Cc2ccc(F)cc2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N(C)c2nc(C)oc2-c2ccc(F)cc2)cc1" ] }, "k": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C)C#Cc2ccc(Br)cc2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N(C)c2nc(C)oc2-c2ccc(Br)cc2)cc1" ] }, "l": { "reactants": [ "CCOc1ccc(C#CN(C)S(=O)(=O)c2ccc(C)cc2)cc1" ], "products": [ "CCOc1ccc(-c2oc(C)nc2N(C)S(=O)(=O)c2ccc(C)cc2)cc1" ] }, "m": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C)C#Cc2ccc(C(C)(C)C)cc2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N(C)c2nc(C)oc2-c2ccc(C(C)(C)C)cc2)cc1" ] }, "n": { "reactants": [ "CCCCc1ccc(C#CN(C)S(=O)(=O)c2ccc(C)cc2)cc1" ], "products": [ "CCCCc1ccc(-c2oc(C)nc2N(C)S(=O)(=O)c2ccc(C)cc2)cc1" ] }, "o": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C)C#Cc2ccc(C#N)cc2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N(C)c2nc(C)oc2-c2ccc(C#N)cc2)cc1" ] }, "p": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C)C#Cc2ccc([N+](=O)[O-])cc2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N(C)c2nc(C)oc2-c2ccc([N+](=O)[O-])cc2)cc1" ] }, "q": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C)C#Cc2cccc(C)c2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N(C)c2nc(C)oc2-c2cccc(C)c2)cc1" ] }, "r": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C)C#Cc2cccc(Cl)c2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N(C)c2nc(C)oc2-c2cccc(Cl)c2)cc1" ] }, "s": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C)C#Cc2cccc(Br)c2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N(C)c2nc(C)oc2-c2cccc(Br)c2)cc1" ] }, "t": { "reactants": [ "COc1ccccc1C#CN(C)S(=O)(=O)c1ccc(C)cc1" ], "products": [ "COc1ccccc1-c1oc(C)nc1N(C)S(=O)(=O)c1ccc(C)cc1" ] }, "u": { "reactants": [ "Cc1ccccc1C#CN(C)S(=O)(=O)c1ccc(C)cc1" ], "products": [ "Cc1ccccc1-c1oc(C)nc1N(C)S(=O)(=O)c1ccc(C)cc1" ] }, "v": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C)C#Cc2cc(Cl)ccc2Cl)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N(C)c2nc(C)oc2-c2cc(Cl)ccc2Cl)cc1" ] }, "w": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C)C#Cc2ccc(c3ccccc3)cc2)cc1" ], "products": [ "c1ccccc1-c1ccc(-c2oc(C)nc2N(C)S(=O)(=O)c2ccc(C)cc2)cc1" ] }, "x": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C)C#Cc2ccc(c3ccc(CC)cc3)cc2)cc1" ], "products": [ "c1cc(CC)ccc1-c1ccc(-c2oc(C)nc2N(C)S(=O)(=O)c2ccc(C)cc2)cc1" ] }, "y": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C)C#Cc2ccc3ccccc3c2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N(C)c2nc(C)oc2-c2ccc3ccccc3c2)cc1" ] }, "z": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C)C#Cc2cccs2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N(C)c2nc(C)oc2-c2cccs2)cc1" ] }, "aa": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C)C#Cc2ccc3sccc3c2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N(C)c2nc(C)oc2-c2ccc3sccc3c2)cc1" ] }, "ab": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C)C#Cc2ccc3occc3c2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N(C)c2nc(C)oc2-c2ccc3occc3c2)cc1" ] }, "ac": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C)C#Cc2ccc(C=O)cc2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N(C)c2nc(C)oc2-c2ccc(C=O)cc2)cc1" ] }, "ad": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C)C#Cc2ccc(C(=O)c3ccccc3)cc2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N(C)c2nc(C)oc2-c2ccc(C(=O)c3ccccc3)cc2)cc1" ] }, "ae": { "reactants": [ "CCCCC#CN(C)S(=O)(=O)c1ccc(C)cc1" ], "products": [ "CCCCc1oc(C)nc1N(C)S(=O)(=O)c1ccc(C)cc1" ] }, "af": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C)C#Cc2ccc(COC(=O)C(C)c3ccc(CC(C)C)cc3)cc2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N(C)c2nc(C)oc2-c2ccc(COC(=O)C(C)c3ccc(CC(C)C)cc3)cc2)cc1" ] }, "ag": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C)C#Cc2cc(CC[C@H]([C@@H](CCC5(=O))[C@@]5(C)CC4)[C@H]34)c3cc2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N(C)c2nc(C)oc2-c2cc(CC[C@H]([C@@H](CCC5(=O))[C@@]5(C)CC4)[C@H]34)c3cc2)cc1" ] } } }, { "file_name": "acs.orglett.2c02717 example 1.png", "reaction_template": { "reactants": [ "c1ccc(C2=Nc3ccccc3OC2)cc1", "*C#CCl" ], "products": [ "*C1=C(Cl)C2(COc3ccccc3N2)c2ccccc21" ] }, "detailed_reactions": { "3aa": { "reactants": [ "c1ccc(C2=Nc3ccccc3OC2)cc1", "ClC#Cc1ccccc1" ], "products": [ "ClC1=C(c2ccccc2)c2ccccc2C12COc1ccccc1N2" ] }, "3ab": { "reactants": [ "c1ccc(C2=Nc3ccccc3OC2)cc1", "Cc1cccc(C#CCl)c1" ], "products": [ "Cc1cccc(C2=C(Cl)C3(COc4ccccc4N3)c3ccccc32)c1" ] }, "3ac 76%": { "reactants": [ "c1ccc(C2=Nc3ccccc3OC2)cc1", "Cc1ccc(C#CCl)cc1" ], "products": [ "Cc1ccc(C2=C(Cl)C3(COc4ccccc4N3)c3ccccc32)cc1" ] }, "3ad": { "reactants": [ "c1ccc(C2=Nc3ccccc3OC2)cc1", "COc1ccc(C#CCl)cc1" ], "products": [ "COc1ccc(C2=C(Cl)C3(COc4ccccc4N3)c3ccccc32)cc1" ] }, "3ae": { "reactants": [ "c1ccc(C2=Nc3ccccc3OC2)cc1", "CCCCC#CCl" ], "products": [ "CCCCC1=C(Cl)C2(COc3ccccc3N2)c2ccccc21" ] }, "3af": { "reactants": [ "c1ccc(C2=Nc3ccccc3OC2)cc1", "FC(F)(F)c1ccc(C#CCl)cc1" ], "products": [ "FC(F)(F)c1ccc(C2=C(Cl)C3(COc4ccccc4N3)c3ccccc32)cc1" ] }, "3ag": { "reactants": [ "c1ccc(C2=Nc3ccccc3OC2)cc1", "CC(C)(C)c1ccc(C#CCl)cc1" ], "products": [ "CC(C)(C)c1ccc(C2=C(Cl)C3(COc4ccccc4N3)c3ccccc32)cc1" ] }, "3ah": { "reactants": [ "c1ccc(C2=Nc3ccccc3OC2)cc1", "CCCCCCC#CCl" ], "products": [ "CCCCCCC1=C(Cl)C2(COc3ccccc3N2)c2ccccc21" ] }, "3ai 68%": { "reactants": [ "c1ccc(C2=Nc3ccccc3OC2)cc1", "ClC#CC1CCCCC1" ], "products": [ "ClC1=C(C2CCCCC2)c2ccccc2C12COc1ccccc1N2" ] }, "3aj": { "reactants": [ "c1ccc(C2=Nc3ccccc3OC2)cc1", "ClC#Cc1ccccc1Cl" ], "products": [ "ClC1=C(c2ccccc2Cl)c2ccccc2C12COc1ccccc1N2" ] }, "3ak": { "reactants": [ "c1ccc(C2=Nc3ccccc3OC2)cc1", "ClC#Cc1cccc(Br)c1" ], "products": [ "ClC1=C(c2cccc(Br)c2)c2ccccc2C12COc1ccccc1N2" ] }, "3al 57%": { "reactants": [ "c1ccc(C2=Nc3ccccc3OC2)cc1", "ClC#Cc1ccc(Cl)cc1" ], "products": [ "ClC1=C(c2ccc(Cl)cc2)c2ccccc2C12COc1ccccc1N2" ] } } }, { "file_name": "acs.orglett.2c03619 example 1.png", "reaction_template": { "reactants": [ "*N(C(=O)C#Cc1ccccc1)C(=O)C(=C)C" ], "products": [ "*N1C(=O)[C@]2(C(=O)c3ccccc3)C[C@]2(C)C1=O" ] }, "detailed_reactions": { "a": { "reactants": [ "C=C(C)C(=O)N(C(=O)C#Cc1ccccc1)c1ccccc1" ], "products": [ "C[C@]12C[C@@]1(C(=O)c1ccccc1)C(=O)N(c1ccccc1)C2=O" ] }, "b": { "reactants": [ "C=C(C)C(=O)N(C(=O)C#Cc1ccccc1)c1ccc(C)cc1" ], "products": [ "C[C@]12C[C@@]1(C(=O)c1ccccc1)C(=O)N(c1ccc(C)cc1)C2=O" ] }, "c": { "reactants": [ "C=C(C)C(=O)N(C(=O)C#Cc1ccccc1)c1ccc(F)cc1" ], "products": [ "C[C@]12C[C@@]1(C(=O)c1ccccc1)C(=O)N(c1ccc(F)cc1)C2=O" ] }, "d": { "reactants": [ "C=C(C)C(=O)N(C(=O)C#Cc1ccccc1)c1ccc(Cl)cc1" ], "products": [ "C[C@]12C[C@@]1(C(=O)c1ccccc1)C(=O)N(c1ccc(Cl)cc1)C2=O" ] }, "e": { "reactants": [ "C=C(C)C(=O)N(C(=O)C#Cc1ccccc1)c1ccc(Br)cc1" ], "products": [ "C[C@]12C[C@@]1(C(=O)c1ccccc1)C(=O)N(c1ccc(Br)cc1)C2=O" ] }, "f": { "reactants": [ "C=C(C)C(=O)N(C(=O)C#Cc1ccccc1)c1ccc(I)cc1" ], "products": [ "C[C@]12C[C@@]1(C(=O)c1ccccc1)C(=O)N(c1ccc(I)cc1)C2=O" ] }, "g": { "reactants": [ "C=C(C)C(=O)N(C(=O)C#Cc1ccccc1)c1ccc(CC(=O)OCC)cc1" ], "products": [ "C[C@]12C[C@@]1(C(=O)c1ccccc1)C(=O)N(c1ccc(CC(=O)OCC)cc1)C2=O" ] }, "h": { "reactants": [ "C=C(C)C(=O)N(C(=O)C#Cc1ccccc1)c1ccc(C(F)(F)F)cc1" ], "products": [ "C[C@]12C[C@@]1(C(=O)c1ccccc1)C(=O)N(c1ccc(C(F)(F)F)cc1)C2=O" ] }, "i": { "reactants": [ "C#Cc1ccc(N(C(=O)C#Cc2ccccc2)C(=O)C(=C)C)cc1" ], "products": [ "C#Cc1ccc(N2C(=O)[C@]3(C(=O)c4ccccc4)C[C@]3(C)C2=O)cc1" ] }, "j": { "reactants": [ "C=C(C)C(=O)N(C(=O)C#Cc1ccccc1)c1ccccc1C" ], "products": [ "Cc1ccccc1N1C(=O)[C@]2(C(=O)c3ccccc3)C[C@]2(C)C1=O" ] }, "k": { "reactants": [ "C=C(C)C(=O)N(C(=O)C#Cc1ccccc1)c1ccc(-c2ccccc2)cc1" ], "products": [ "C[C@]12C[C@@]1(C(=O)c1ccccc1)C(=O)N(c1ccc(-c3ccccc3)cc1)C2=O" ] }, "l": { "reactants": [ "C=C(C)C(=O)N(C(=O)C#Cc1ccccc1)c1cc(C)cc(C)c1" ], "products": [ "Cc1cc(C)cc(N2C(=O)[C@]3(C(=O)c4ccccc4)C[C@]3(C)C2=O)c1" ] }, "m": { "reactants": [ "C=C(C)C(=O)N(C(=O)C#Cc1ccccc1)c1cc(C)c(C)c(C)c1" ], "products": [ "Cc1c(C)c(C)cc(N2C(=O)[C@]3(C(=O)c4ccccc4)C[C@]3(C)C2=O)c1" ] }, "n": { "reactants": [ "C=C(C)C(=O)N(Cc1ccccc1)C(=O)C#Cc1ccccc1" ], "products": [ "C[C@]12C[C@@]1(C(=O)c1ccccc1)C(=O)N(Cc1ccccc1)C2=O" ] }, "o": { "reactants": [ "C=C(C)C(=O)N(CCc1ccc(OC)c(OC)c1)C(=O)C#Cc1ccccc1" ], "products": [ "COc1ccc(CCN2C(=O)[C@]3(C(=O)c4ccccc4)C[C@]3(C)C2=O)cc1OC" ] }, "p": { "reactants": [ "C=C(C)C(=O)N(CCCC)C(=O)C#Cc1ccccc1" ], "products": [ "CCCCN1C(=O)[C@]2(C(=O)c3ccccc3)C[C@]2(C)C1=O" ] } } }, { "file_name": "acs.orglett.2c03765 example 1.png", "reaction_template": { "reactants": [ "O=C1CCCCC1c1ccccn1", "*B1OCC(C)(C)CO1" ], "products": [ "*C1=C(c2ccccn2)CCCC1" ] }, "detailed_reactions": { "aa": { "reactants": [ "O=C1CCCCC1c1ccccn1", "CC1(C)COB(c2ccccc2)OC1" ], "products": [ "c1ccc(C2=C(c3ccccn3)CCCC2)cc1" ] }, "ab": { "reactants": [ "O=C1CCCCC1c1ccccn1", "C=Cc1ccc(B2OCC(C)(C)CO2)cc1" ], "products": [ "C=Cc1ccc(C2=C(c3ccccn3)CCCC2)cc1" ] }, "ac": { "reactants": [ "O=C1CCCCC1c1ccccn1", "CC1(C)COB(c2ccc3ccccc3c2)OC1" ], "products": [ "c1ccc(C2=C(c3ccc4ccccc4c3)CCCC2)nc1" ] }, "ad": { "reactants": [ "O=C1CCCCC1c1ccccn1", "CC1(C)COB(c2ccc(-c3ccccc3)cc2)OC1" ], "products": [ "c1ccc(-c2ccc(C3=C(c4ccccn4)CCCC3)cc2)cc1" ] }, "ae": { "reactants": [ "O=C1CCCCC1c1ccccn1", "Cc1ccc(B2OCC(C)(C)CO2)cc1" ], "products": [ "Cc1ccc(C2=C(c3ccccn3)CCCC2)cc1" ] }, "af": { "reactants": [ "O=C1CCCCC1c1ccccn1", "COc1ccc(B2OCC(C)(C)CO2)cc1" ], "products": [ "COc1ccc(C2=C(c3ccccn3)CCCC2)cc1" ] }, "ag": { "reactants": [ "O=C1CCCCC1c1ccccn1", "CN(C)c1ccc(B2OCC(C)(C)CO2)cc1" ], "products": [ "CN(C)c1ccc(C2=C(c3ccccn3)CCCC2)cc1" ] }, "ah": { "reactants": [ "O=C1CCCCC1c1ccccn1", "CC1(C)COB(c2ccc(F)cc2)OC1" ], "products": [ "Fc1ccc(C2=C(c3ccccn3)CCCC2)cc1" ] }, "ai": { "reactants": [ "O=C1CCCCC1c1ccccn1", "CC1(C)COB(c2ccc(Cl)cc2)OC1" ], "products": [ "Clc1ccc(C2=C(c3ccccn3)CCCC2)cc1" ] }, "aj": { "reactants": [ "O=C1CCCCC1c1ccccn1", "CC1(C)COB(c2ccc(C(F)(F)F)cc2)OC1" ], "products": [ "FC(F)(F)c1ccc(C2=C(c3ccccn3)CCCC2)cc1" ] }, "ak": { "reactants": [ "O=C1CCCCC1c1ccccn1", "CC(=O)c1ccc(B2OCC(C)(C)CO2)cc1" ], "products": [ "CC(=O)c1ccc(C2=C(c3ccccn3)CCCC2)cc1" ] }, "al": { "reactants": [ "O=C1CCCCC1c1ccccn1", "CC1(C)COB(c2ccc(C(=O)c3ccccc3)cc2)OC1" ], "products": [ "O=C(c1ccccc1)c1ccc(C2=C(c3ccccn3)CCCC2)cc1" ] }, "am": { "reactants": [ "O=C1CCCCC1c1ccccn1", "COC(=O)c1ccc(B2OCC(C)(C)CO2)cc1" ], "products": [ "COC(=O)c1ccc(C2=C(c3ccccn3)CCCC2)cc1" ] }, "an": { "reactants": [ "O=C1CCCCC1c1ccccn1", "CCOC(=O)c1ccc(B2OCC(C)(C)CO2)cc1" ], "products": [ "CCOC(=O)c1ccc(C2=C(c3ccccn3)CCCC2)cc1" ] }, "ao": { "reactants": [ "O=C1CCCCC1c1ccccn1", "CC(C)OC(=O)c1ccc(B2OCC(C)(C)CO2)cc1" ], "products": [ "CC(C)OC(=O)c1ccc(C2=C(c3ccccn3)CCCC2)cc1" ] }, "ap": { "reactants": [ "O=C1CCCCC1c1ccccn1", "CCN(CC)C(=O)c1ccc(B2OCC(C)(C)CO2)cc1" ], "products": [ "CCN(CC)C(=O)c1ccc(C2=C(c3ccccn3)CCCC2)cc1" ] }, "aq": { "reactants": [ "O=C1CCCCC1c1ccccn1", "CC1(C)COB(c2ccc(C#N)cc2)OC1" ], "products": [ "N#Cc1ccc(C2=C(c3ccccn3)CCCC2)cc1" ] }, "ar": { "reactants": [ "O=C1CCCCC1c1ccccn1", "CC1(C)COB(c2cccs2)OC1" ], "products": [ "c1ccc(C2=C(c3cccs3)CCCC2)nc1" ] } } }, { "file_name": "acs.orglett.2c03800 example 1.png", "reaction_template": { "reactants": [ "C[C@H](C(=O)N1C(=S)SC[C@@H]1Cc1ccccc1)[C@H](O)[Rf]" ], "products": [ "C[C@@H]1CC(=O)O[C@@H]1[Rf]" ] }, "detailed_reactions": { "a": { "reactants": [ "Cc1ccc([C@@H](O)[C@H](C)C(=O)N2C(=S)SC[C@@H]2Cc2ccccc2)cc1" ], "products": [ "Cc1ccc([C@H]2OC(=O)C[C@H]2C)cc1" ] }, "b": { "reactants": [ "COc1ccc([C@@H](O)[C@H](C)C(=O)N2C(=S)SC[C@@H]2Cc2ccccc2)cc1" ], "products": [ "COc1ccc([C@H]2OC(=O)C[C@H]2C)cc1" ] }, "c": { "reactants": [ "COc1cc([C@@H](O)[C@H](C)C(=O)N2C(=S)SC[C@@H]2Cc2ccccc2)cc(OC)c1OC" ], "products": [ "COc1cc([C@H]2OC(=O)C[C@H]2C)cc(OC)c1OC" ] }, "d": { "reactants": [ "C[C@H](C(=O)N1C(=S)SC[C@@H]1Cc1ccccc1)[C@H](O)c1ccc(F)cc1" ], "products": [ "C[C@@H]1CC(=O)O[C@@H]1c1ccc(F)cc1" ] }, "e": { "reactants": [ "COc1cc([C@@H](O)[C@H](C)C(=O)N2C(=S)SC[C@@H]2Cc2ccccc2)ccc1F" ], "products": [ "COc1cc([C@H]2OC(=O)C[C@H]2C)ccc1F" ] }, "f": { "reactants": [ "C[C@H](C(=O)N1C(=S)SC[C@@H]1Cc1ccccc1)[C@H](O)c1ccc(Cl)cc1" ], "products": [ "C[C@@H]1CC(=O)O[C@@H]1c1ccc(Cl)cc1" ] }, "g": { "reactants": [ "C[C@H](C(=O)N1C(=S)SC[C@@H]1Cc1ccccc1)[C@H](O)c1ccc2ccccc2c1" ], "products": [ "C[C@H]1CC(=O)O[C@@H]1c1ccc2ccccc2c1" ] }, "h": { "reactants": [ "COc1ccc2cc([C@@H](O)[C@H](C)C(=O)N3C(=S)SC[C@@H]3Cc3ccccc3)ccc2c1" ], "products": [ "COc1ccc2cc([C@H]3OC(=O)C[C@@H]3C)ccc2c1" ] }, "i": { "reactants": [ "C[C@H](C(=O)N1C(=S)SC[C@@H]1Cc1ccccc1)[C@H](O)c1cccs1" ], "products": [ "C[C@@H]1CC(=O)O[C@@H]1c1cccs1" ] }, "j": { "reactants": [ "C[C@H](C(=O)N1C(=S)SC[C@@H]1Cc1ccccc1)[C@H](O)c1ccco1" ], "products": [ "C[C@@H]1CC(=O)O[C@@H]1c1ccco1" ] }, "k": { "reactants": [ "CCCC[C@@H](O)[C@H](C)C(=O)N2C(=S)SC[C@@H]2Cc2ccccc2" ], "products": [ "CCCC[C@H]2OC(=O)C[C@H]2C" ] }, "l": { "reactants": [ "CCCCC[C@@H](O)[C@H](C)C(=O)N2C(=S)SC[C@@H]2Cc2ccccc2" ], "products": [ "CCCCC[C@H]2OC(=O)C[C@H]2C" ] }, "m": { "reactants": [ "CCCCCCC[C@@H](O)[C@H](C)C(=O)N2C(=S)SC[C@@H]2Cc2ccccc2" ], "products": [ "CCCCCCC[C@H]2OC(=O)C[C@H]2C" ] }, "n": { "reactants": [ "CC(C)c1ccc([C@@H](O)[C@H](C)C(=O)N2C(=S)SC[C@@H]2Cc2ccccc2)cc1" ], "products": [ "CC(C)c1ccc([C@H]2OC(=O)C[C@H]2C)cc1" ] }, "o": { "reactants": [ "CC(C)Cc1ccc([C@@H](O)[C@H](C)C(=O)N2C(=S)SC[C@@H]2Cc2ccccc2)cc1" ], "products": [ "CC(C)Cc1ccc([C@H]2OC(=O)C[C@H]2C)cc1" ] }, "p": { "reactants": [ "C[C@H](C(=O)N1C(=S)SC[C@@H]1Cc1ccccc1)[C@H](O)c1ccc(F)c(F)c1" ], "products": [ "C[C@@H]1CC(=O)O[C@@H]1c1ccc(F)c(F)c1" ] }, "q": { "reactants": [ "C[C@H](C(=O)N1C(=S)SC[C@@H]1Cc1ccccc1)[C@H](O)c1cc(F)cc(F)c1" ], "products": [ "C[C@@H]1CC(=O)O[C@@H]1c1cc(F)cc(F)c1" ] }, "r": { "reactants": [ "C[C@H](C(=O)N1C(=S)SC[C@@H]1Cc1ccccc1)[C@H](O)c1ccc([N+](=O)[O-])cc1" ], "products": [ "C[C@@H]1CC(=O)O[C@@H]1c1ccc([N+](=O)[O-])cc1" ] }, "s": { "reactants": [ "C[C@H](C(=O)N1C(=S)SC[C@@H]1Cc1ccccc1)[C@H](O)c1ccc(C#N)cc1" ], "products": [ "C[C@@H]1CC(=O)O[C@@H]1c1ccc(C#N)cc1" ] }, "t": { "reactants": [ "COc1ccc([C@@H](O)[C@H](C)C(=O)N2C(=S)SC[C@@H]2Cc2ccccc2)cc1[N+](=O)[O-]" ], "products": [ "COc1ccc([C@H]2OC(=O)C[C@H]2C)cc1[N+](=O)[O-]" ] } } }, { "file_name": "acs.orglett.2c03900 example 1.png", "reaction_template": { "reactants": [ "*c1nnn(C(=C)C(F)(F)F)n1", "COc1ccc(CN)cc1" ], "products": [ "*c1nnn(C(CNCc2ccc(OC)cc2)C(F)(F)F)n1" ] }, "detailed_reactions": { "a": { "reactants": [ "C=C(n1nnc(-c2ccccc2)n1)C(F)(F)F", "COc1ccc(CN)cc1" ], "products": [ "COc1ccc(CNCC(n2nnc(-c3ccccc3)n2)C(F)(F)F)cc1" ] }, "b": { "reactants": [ "C=C(n1nnc(-c2ccc(Cl)cc2)n1)C(F)(F)F", "COc1ccc(CN)cc1" ], "products": [ "COc1ccc(CNCC(n2nnc(-c3ccc(Cl)cc3)n2)C(F)(F)F)cc1" ] }, "c": { "reactants": [ "C=C(n1nnc(-c2ccc(C)cc2)n1)C(F)(F)F", "COc1ccc(CN)cc1" ], "products": [ "COc1ccc(CNCC(n2nnc(-c3ccc(C)cc3)n2)C(F)(F)F)cc1" ] }, "d": { "reactants": [ "C=C(n1nnc(-c2cccc([N+](=O)[O-])c2)n1)C(F)(F)F", "COc1ccc(CN)cc1" ], "products": [ "COc1ccc(CNCC(n2nnc(-c3cccc([N+](=O)[O-])c3)n2)C(F)(F)F)cc1" ] }, "e": { "reactants": [ "C=C(n1nnc(-c2ccc3ccccc3c2)n1)C(F)(F)F", "COc1ccc(CN)cc1" ], "products": [ "COc1ccc(CNCC(n2nnc(-c3ccc4ccccc4c3)n2)C(F)(F)F)cc1" ] }, "f": { "reactants": [ "C=C(n1nnc(-c2ccsc2)n1)C(F)(F)F", "COc1ccc(CN)cc1" ], "products": [ "COc1ccc(CNCC(n2nnc(-c3ccsc3)n2)C(F)(F)F)cc1" ] }, "g": { "reactants": [ "C=C(n1nnc(-c2cnccn2)n1)C(F)(F)F", "COc1ccc(CN)cc1" ], "products": [ "COc1ccc(CNCC(n2nnc(-c3cnccn3)n2)C(F)(F)F)cc1" ] }, "h": { "reactants": [ "C=C(n1nnc(C=Cc2ccccc2)n1)C(F)(F)F", "COc1ccc(CN)cc1" ], "products": [ "COc1ccc(CNCC(n2nnc(C=Cc3ccccc3)n2)C(F)(F)F)cc1" ] }, "i": { "reactants": [ "C=C(n1nnc(-c2cc(C)ccc2)n1)C(F)(F)F", "COc1ccc(CN)cc1" ], "products": [ "COc1ccc(CNCC(n2nnc(-c3cc(C)ccc3)n2)C(F)(F)F)cc1" ] }, "j": { "reactants": [ "C=C(n1nnc(CCCC)n1)C(F)(F)F", "COc1ccc(CN)cc1" ], "products": [ "CCCCc1nnn(C(CNCc2ccc(OC)cc2)C(F)(F)F)n1" ] }, "k": { "reactants": [ "C=C(n1nnc(SCc2ccccc2)n1)C(F)(F)F", "COc1ccc(CN)cc1" ], "products": [ "COc1ccc(CNCC(n2nnc(SCc3ccccc3)n2)C(F)(F)F)cc1" ] }, "l": { "reactants": [ "C=C(n1nnc(C(=O)OCC)n1)C(F)(F)F", "COc1ccc(CN)cc1" ], "products": [ "CCOC(=O)c1nnn(C(CNCc2ccc(OC)cc2)C(F)(F)F)n1" ] }, "m": { "reactants": [ "C(=C)(n2nnn(C)c2=S)C(F)(F)F", "COc1ccc(CN)cc1" ], "products": [ "COc1ccc(CNCC(n2nnn(C)c2=S)C(F)(F)F)cc1" ] } } }, { "file_name": "acs.joc.3c00690 example 1.png", "reaction_template": { "reactants": [ "[1*]C(=O)CN(C([2*])C([3*])O[Si](C)(C)C(C)(C)C)S(=O)(=O)c1ccc(C)cc1" ], "products": [ "[1*]C(=O)C1OC([3*])C([2*])N1S(=O)(=O)c1ccc(C)cc1" ] }, "detailed_reactions": { "b": { "reactants": [ "Cc1ccc(C(=O)CN(CCO[Si](C)(C)C(C)(C)C)S(=O)(=O)c2ccc(C)cc2)cc1" ], "products": [ "Cc1ccc(C(=O)C2OCCN2S(=O)(=O)c2ccc(C)cc2)cc1" ] }, "c": { "reactants": [ "COc1ccc(C(=O)CN(CCO[Si](C)(C)C(C)(C)C)S(=O)(=O)c2ccc(C)cc2)cc1" ], "products": [ "COc1ccc(C(=O)C2OCCN2S(=O)(=O)c2ccc(C)cc2)cc1" ] }, "d": { "reactants": [ "COc1ccccc1C(=O)CN(CCO[Si](C)(C)C(C)(C)C)S(=O)(=O)c1ccc(C)cc1" ], "products": [ "COc1ccccc1C(=O)C1OCCN1S(=O)(=O)c1ccc(C)cc1" ] }, "e": { "reactants": [ "Cc1ccc(S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CC(=O)c2ccc(F)cc2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N2CCOC2C(=O)c2ccc(F)cc2)cc1" ] }, "f": { "reactants": [ "Cc1ccc(S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CC(=O)c2ccc(Cl)cc2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N2CCOC2C(=O)c2ccc(Cl)cc2)cc1" ] }, "g": { "reactants": [ "Cc1ccc(S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CC(=O)c2ccc(Br)cc2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N2CCOC2C(=O)c2ccc(Br)cc2)cc1" ] }, "h": { "reactants": [ "Cc1ccc(S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CC(=O)c2c(F)cccc2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N2CCOC2C(=O)c2c(F)cccc2)cc1" ] }, "i": { "reactants": [ "Cc1ccc(S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CC(=O)c2cccc(Cl)c2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N2CCOC2C(=O)c2cccc(Cl)c2)cc1" ] }, "j": { "reactants": [ "Cc1ccc(S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CC(=O)c2ccc(C#N)cc2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N2CCOC2C(=O)c2ccc(C#N)cc2)cc1" ] }, "k": { "reactants": [ "Cc1ccc(S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CC(=O)c2cccs2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N2CCOC2C(=O)c2cccs2)cc1" ] }, "l": { "reactants": [ "Cc1ccc(S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CC(=O)c2ccco2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N2CCOC2C(=O)c2ccco2)cc1" ] }, "m": { "reactants": [ "Cc1ccc(S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CC(=O)c2cccc(-c3ccccc3)c2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N2CCOC2C(=O)c2cccc(-c3ccccc3)c2)cc1" ] }, "n": { "reactants": [ "Cc1ccc(S(=O)(=O)N(CCO[Si](C)(C)C(C)(C)C)CC(=O)c2cc3ccccc3cc2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N2CCOC2C(=O)c2ccc3ccccc3c2)cc1" ] }, "o": { "reactants": [ "CC(=O)CN(CCO[Si](C)(C)C(C)(C)C)S(=O)(=O)c1ccc(C)cc1" ], "products": [ "CC(=O)C1OCCN1S(=O)(=O)c1ccc(C)cc1" ] }, "p": { "reactants": [ "Cc1ccc(S(=O)(=O)N(CC(=O)c2ccccc2)C(CO[Si](C)(C)C(C)(C)C)c2ccccc2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N2C(C(=O)c3ccccc3)OCC2c2ccccc2)cc1" ] }, "q": { "reactants": [ "Cc1ccc(S(=O)(=O)N(CC(=O)c2ccccc2)C(CO[Si](C)(C)C(C)(C)C)Cc2ccccc2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N2C(Cc3ccccc3)COC2C(=O)c2ccccc2)cc1" ] }, "r": { "reactants": [ "Cc1ccc(S(=O)(=O)N(CC(=O)c2ccccc2)C(C)CO[Si](C)(C)C(C)(C)C)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N2C(C)COC2C(=O)c2ccccc2)cc1" ] }, "s": { "reactants": [ "CCC(CO[Si](C)(C)C(C)(C)C)N(CC(=O)c1ccccc1)S(=O)(=O)c1ccc(C)cc1" ], "products": [ "CCC1COC(C(=O)c2ccccc2)N1S(=O)(=O)c1ccc(C)cc1" ] }, "t": { "reactants": [ "C(C(C)O[Si](C)(C)C(C)(C)C)N(CC(=O)c1ccccc1)S(=O)(=O)c1ccc(C)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N2CC(C)OC2C(=O)c2ccccc2)cc1" ] }, "u": { "reactants": [ "Cc1ccc(S(=O)(=O)N(CCCO[Si](C)(C)C(C)(C)C)CC(=O)c2ccccc2)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)N2CCCOC2C(=O)c2ccccc2)cc1" ] } } }, { "file_name": "10.1002:anie.202314701 example 1.png", "reaction_template": { "reactants": [ "O=P1(c2ccccc2)c2ccccc2-c2ccccc21", "*C#C*" ], "products": [ "*C1=C(*)P(=O)(c2ccccc2)c2ccccc2-c2ccccc21" ] }, "detailed_reactions": { "a": { "reactants": [ "O=P1(c2ccccc2)c2ccccc2-c2ccccc21", "CCCC#CCCC" ], "products": [ "CCCC1=C(CCC)P(=O)(c2ccccc2)c2ccccc2-c2ccccc21" ] }, "b": { "reactants": [ "O=P1(c2ccccc2)c2ccccc2-c2ccccc21", "CCC#CCC" ], "products": [ "CCC1=C(CC)P(=O)(c2ccccc2)c2ccccc2-c2ccccc21" ] }, "c": { "reactants": [ "O=P1(c2ccccc2)c2ccccc2-c2ccccc21", "CCCCC#CCCCC" ], "products": [ "CCCCC1=C(CCCC)P(=O)(c2ccccc2)c2ccccc2-c2ccccc21" ] }, "d": { "reactants": [ "O=P1(c2ccccc2)c2ccccc2-c2ccccc21", "CC(C)CCC#CCCC(C)C" ], "products": [ "CC(C)CCC1=C(CCC(C)C)P(=O)(c2ccccc2)c2ccccc2-c2ccccc21" ] }, "e": { "reactants": [ "O=P1(c2ccccc2)c2ccccc2-c2ccccc21", "CCCCCCC#CCCCCCC" ], "products": [ "CCCCCCC1=C(CCCCCC)P(=O)(c2ccccc2)c2ccccc2-c2ccccc21" ] }, "f": { "reactants": [ "O=P1(c2ccccc2)c2ccccc2-c2ccccc21", "CC(C)(C)[Si](C)(C)OCCCC#CCCCO[Si](C)(C)C(C)(C)C" ], "products": [ "CC(C)(C)[Si](C)(C)CCCC1=C(CCCO[Si](C)(C)C(C)(C)C)P(=O)(c2ccccc2)c2ccccc2-c2ccccc21" ] }, "g": { "reactants": [ "O=P1(c2ccccc2)c2ccccc2-c2ccccc21", "C(#Cc1ccccc1)c1ccccc1" ], "products": [ "O=P1(c2ccccc2)C(c2ccccc2)=C(c2ccccc2)c2ccccc2-c2ccccc21" ] }, "h": { "reactants": [ "O=P1(c2ccccc2)c2ccccc2-c2ccccc21", "Cc1ccc(C#Cc2ccc(C)cc2)cc1" ], "products": [ "Cc1ccc(C2=C(c3ccc(C)cc3)P(=O)(c3ccccc3)c3ccccc3-c3ccccc32)cc1" ] }, "i": { "reactants": [ "O=P1(c2ccccc2)c2ccccc2-c2ccccc21", "CC(C)(C)c1ccc(C#Cc2ccc(C(C)(C)C)cc2)cc1" ], "products": [ "CC(C)(C)c1ccc(C2=C(c3ccc(C(C)(C)C)cc3)P(=O)(c3ccccc3)c3ccccc3-c3ccccc32)cc1" ] }, "j": { "reactants": [ "O=P1(c2ccccc2)c2ccccc2-c2ccccc21", "COc1ccc(C#Cc2ccc(OC)cc2)cc1" ], "products": [ "COc1ccc(C2=C(c3ccc(OC)cc3)P(=O)(c3ccccc3)c3ccccc3-c3ccccc32)cc1" ] }, "k": { "reactants": [ "O=P1(c2ccccc2)c2ccccc2-c2ccccc21", "FC(F)(F)Oc1ccc(C#Cc2ccc(OC(F)(F)F)cc2)cc1" ], "products": [ "FC(F)(F)Oc1ccc(C2=C(c3ccc(OC(F)(F)F)cc3)P(=O)(c3ccccc3)c3ccccc3-c3ccccc32)cc1" ] }, "l": { "reactants": [ "O=P1(c2ccccc2)c2ccccc2-c2ccccc21", "C[Si](C)(C)c1ccc(C#Cc2ccc([Si](C)(C)C)cc2)cc1" ], "products": [ "C[Si](C)(C)c1ccc(C2=C(c3ccc([Si](C)(C)C)cc3)P(=O)(c3ccccc3)c3ccccc3-c3ccccc32)cc1" ] }, "m": { "reactants": [ "O=P1(c2ccccc2)c2ccccc2-c2ccccc21", "Fc1ccc(C#Cc2ccc(F)cc2)cc1" ], "products": [ "Fc1ccc(C2=C(c3ccc(F)cc3)P(=O)(c3ccccc3)c3ccccc3-c3ccccc32)cc1" ] }, "n": { "reactants": [ "O=P1(c2ccccc2)c2ccccc2-c2ccccc21", "FC(F)(F)c1ccc(C#Cc2ccc(C(F)(F)F)cc2)cc1" ], "products": [ "*c1ccc(C2=C(c3ccc(*)cc3)P(=O)(c3ccccc3)c3ccccc3-c3ccccc32)cc1" ] }, "o": { "reactants": [ "O=P1(c2ccccc2)c2ccccc2-c2ccccc21", "Cc1cccc(C#Cc2cccc(C)c2)c1" ], "products": [ "Cc1cccc(C2=C(c3cccc(C)c3)P(=O)(c3ccccc3)c3ccccc3-c3ccccc32)c1" ] }, "p": { "reactants": [ "O=P1(c2ccccc2)c2ccccc2-c2ccccc21", "Fc1cccc(C#Cc2cccc(F)c2)c1" ], "products": [ "Fc1cccc(C2=C(c3cccc(F)c3)P(=O)(c3ccccc3)c3ccccc3-c3ccccc32)c1" ] }, "q": { "reactants": [ "O=P1(c2ccccc2)c2ccccc2-c2ccccc21", "FC(F)(F)Oc1cccc(C#Cc2cccc(OC(F)(F)F)c2)c1" ], "products": [ "FC(F)(F)c1cccc(C2=C(c3cccc(OC(F)(F)F)c3)P(=O)(c3ccccc3)c3ccccc3-c3ccccc32)c1" ] }, "r": { "reactants": [ "O=P1(c2ccccc2)c2ccccc2-c2ccccc21", "COC(=O)c1cccc(C#Cc2cccc(C(=O)OC)c2)c1" ], "products": [ "COC(=O)c1cccc(C2=C(c3cccc(C(=O)OC)c3)P(=O)(c3ccccc3)c3ccccc3-c3ccccc32)c1" ] }, "s": { "reactants": [ "O=P1(c2ccccc2)c2ccccc2-c2ccccc21", "Fc1ccccc1C#Cc1ccccc1F" ], "products": [ "O=P1(c2ccccc2)C(c2ccccc2F)=C(c2ccccc2F)c2ccccc2-c2ccccc21" ] }, "t": { "reactants": [ "O=P1(c2ccccc2)c2ccccc2-c2ccccc21", "Cn1ccc2ccc(C#Cc3ccc4ccn(C)c4c3)cc21" ], "products": [ "Cn1ccc2ccc(C3=C(c4ccc5ccn(C)c5c4)P(=O)(c4ccccc4)c4ccccc4-c4ccccc43)cc21" ] }, "u": { "reactants": [ "O=P1(c2ccccc2)c2ccccc2-c2ccccc21", "Cc1ccc(C#Cc2ccc(C)c(C)c2)cc1C" ], "products": [ "Cc1ccc(C2=C(c3ccc(C)c(C)c3)P(=O)(c3ccccc3)c3ccccc3-c3ccccc32)cc1C" ] }, "v": { "reactants": [ "O=P1(c2ccccc2)c2ccccc2-c2ccccc21", "C(#CC[Si](C)(C))c1ccccc1" ], "products": [ "C[Si](C)(C)C1=C(c2ccccc2)c2ccccc2-c2ccccc2P1(=O)c1ccccc1" ] }, "w": { "reactants": [ "O=P1(c2ccccc2)c2ccccc2-c2ccccc21", "C(#CC(C)(C)C)c1ccccc1" ], "products": [ "CC(C)(C)C1=C(c2ccccc2)c2ccccc2-c2ccccc2P1(=O)c1ccccc1" ] }, "x": { "reactants": [ "O=P1(c2ccccc2)c2ccccc2-c2ccccc21", "C[Si](C)(C)C#CC" ], "products": [ "CC1=C([Si](C)(C)C)c2ccccc2-c2ccccc2P1(=O)c1ccccc1" ] } } }, { "file_name": "10.1002:anie.202313578 example 1.png", "reaction_template": { "reactants": [ "*/N=N/*" ], "products": [ "*N([H])N(*)[H]" ] }, "detailed_reactions": { "a": { "reactants": [ "c1ccc(N=Nc2ccccc2)cc1" ], "products": [ "c1ccc(NNc2ccccc2)cc1" ] }, "b": { "reactants": [ "Cc1ccc(N=Nc2ccc(C)cc2)cc1" ], "products": [ "Cc1ccc(NNc2ccc(C)cc2)cc1" ] }, "e": { "reactants": [ "Brc1ccc(N=Nc2ccc(Br)cc2)cc1" ], "products": [ "Brc1ccc(NNc2ccc(Br)cc2)cc1" ] }, "f": { "reactants": [ "FC(F)(F)c1ccc(N=Nc2ccc(C(F)(F)F)cc2)cc1" ], "products": [ "FC(F)(F)c1ccc(NNc2ccc(C(F)(F)F)cc2)cc1" ] }, "g": { "reactants": [ "Cc1cc(C)cc(N=Nc2cc(C)cc(C)c2)c1" ], "products": [ "Cc1cc(C)cc(NNc2cc(C)cc(C)c2)c1" ] }, "h": { "reactants": [ "c1ccc2c(c1)CCc1ccccc1N=N2" ], "products": [ "c1ccc2c(c1)CCc1ccccc1NN2" ] } } }, { "file_name": "ejoc202301095 example 1.png", "reaction_template": { "reactants": [ "*C(*)=O", "C1CCNC1", "[H]C#Cc1ccccc1" ], "products": [ "[1*]C([2*])(C#Cc1ccccc1)N1CCCC1" ] }, "detailed_reactions": { "c": { "reactants": [ "C1CCC(=O)C1", "C1CCNC1", "C#Cc1ccccc1" ], "products": [ "C(#CC1(N2CCCC2)CCCC1)c1ccccc1" ] }, "d": { "reactants": [ "C1CCCCC(=O)CCCCCCC1", "C1CCNC1", "C#Cc1ccccc1" ], "products": [ "C(#CC1(N2CCCC2)CCCCCCCCCCC1)c1ccccc1" ] }, "e": { "reactants": [ "CCCC(C)=O", "C1CCNC1", "C#Cc1ccccc1" ], "products": [ "CCCC(C)(C#Cc1ccccc1)N1CCCC1" ] }, "f": { "reactants": [ "CCC(=O)CC", "C1CCNC1", "C#Cc1ccccc1" ], "products": [ "CCC(C#Cc1ccccc1)(CC)N1CCCC1" ] }, "g": { "reactants": [ "CCCCCCC(=O)CCC", "C1CCNC1", "C#Cc1ccccc1" ], "products": [ "CCCCCCC(C#Cc1ccccc1)(CCC)N1CCCC1" ] }, "h": { "reactants": [ "C1=CC(=O)CCC1", "C1CCNC1", "C#Cc1ccccc1" ], "products": [ "C(#CC1(N2CCCC2)C=CCCC1)c1ccccc1" ] }, "i": { "reactants": [ "CC(=O)c1ccccc1", "C1CCNC1", "C#Cc1ccccc1" ], "products": [ "CC(C#Cc1ccccc1)(c1ccccc1)N1CCCC1" ] }, "j": { "reactants": [ "CC(=O)c1ccc(Cl)cc1", "C1CCNC1", "C#Cc1ccccc1" ], "products": [ "CC(C#Cc1ccccc1)(c1ccc(Cl)cc1)N1CCCC1" ] } } }, { "file_name": "ejoc202301095 example 2.png", "reaction_template": { "reactants": [ "O=C1CCCCC1", "C1CCNC1", "[5*]C#C[H]" ], "products": [ "[5*]C#CC1(N2CCCC2)CCCCC1" ] }, "detailed_reactions": { "k": { "reactants": [ "O=C1CCCCC1", "C1CCNC1", "C#Cc1ccc(C)cc1" ], "products": [ "Cc1ccc(C#CC2(N3CCCC3)CCCCC2)cc1" ] }, "l": { "reactants": [ "O=C1CCCCC1", "C1CCNC1", "C#Cc1ccc(OC)cc1" ], "products": [ "COc1ccc(C#CC2(N3CCCC3)CCCCC2)cc1" ] }, "m": { "reactants": [ "O=C1CCCCC1", "C1CCNC1", "C#Cc1ccc(Cl)cc1" ], "products": [ "Clc1ccc(C#CC2(N3CCCC3)CCCCC2)cc1" ] }, "n": { "reactants": [ "O=C1CCCCC1", "C1CCNC1", "C#Cc1ccc(C(F)(F)F)cc1" ], "products": [ "FC(F)(F)c1ccc(C#CC2(N3CCCC3)CCCCC2)cc1" ] }, "o": { "reactants": [ "O=C1CCCCC1", "C1CCNC1", "C#Cc1ccc([N+](=O)[O-])cc1" ], "products": [ "O=[N+]([O-])c1ccc(C#CC2(N3CCCC3)CCCCC2)cc1" ] }, "p": { "reactants": [ "O=C1CCCCC1", "C1CCNC1", "C#CCCCCCC" ], "products": [ "C(#CC1(N2CCCC2)CCCCC1)CCCCCC" ] }, "q": { "reactants": [ "O=C1CCCCC1", "C1CCNC1", "C#CCCc1ccccc1" ], "products": [ "C(#CC1(N2CCCC2)CCCCC1)CCc1ccccc1" ] }, "r": { "reactants": [ "O=C1CCCCC1", "C1CCNC1", "C#CCc1ccccc1" ], "products": [ "C(#CC1(N2CCCC2)CCCCC1)Cc1ccccc1" ] }, "s": { "reactants": [ "O=C1CCCCC1", "C1CCNC1", "C#CC1CCCCC1" ], "products": [ "C(#CC1(N2CCCC2)CCCCC1)C1CCCCC1" ] } } }, { "file_name": "ejoc202301095 example 3.png", "reaction_template": { "reactants": [ "*C(*)=O", "[3*]N[4*]", "[H]C#Cc1ccccc1" ], "products": [ "[1*]C([2*])(C#Cc1ccccc1)N[3*]" ] }, "detailed_reactions": { "b": { "reactants": [ "C1CC(=O)CCC1", "C1NCCCC1", "C#Cc1ccccc1" ], "products": [ "C(#CC1(N2CCCCC2)CCCCC1)c1ccccc1" ] }, "t": { "reactants": [ "CC(=O)CCC", "C1NCCCC1", "C#Cc1ccccc1" ], "products": [ "CCCC(C)(C#Cc1ccccc1)N1CCCCC1" ] }, "u": { "reactants": [ "C1CC(=O)CCC1", "C1NCCOC1", "C#Cc1ccccc1" ], "products": [ "C(#CC1(N2CCOCC2)CCCCC1)c1ccccc1" ] }, "v": { "reactants": [ "C1CC(=O)CCC1", "c1ccccc1CCN", "C#Cc1ccccc1" ], "products": [ "C(#CC1(NCc2ccccc2)CCCCC1)c1ccccc1" ] }, "w": { "reactants": [ "C1CC(=O)CCC1", "NCCCCCCCC", "C#Cc1ccccc1" ], "products": [ "CCCCCCCCNC1(C#Cc2ccccc2)CCCCC1" ] }, "x": { "reactants": [ "C1CC(=O)CCC1", "CCCNCCC", "C#Cc1ccccc1" ], "products": [ "CCCN(CCC)C1(C#Cc2ccccc2)CCCCC1" ] }, "y": { "reactants": [ "CC(=O)CCC", "C1CCCCC1NC", "C#Cc1ccccc1" ], "products": [ "CCCC(C)(C#Cc1ccccc1)N(C)C1CCCCC1" ] }, "z": { "reactants": [ "C1CC(=O)CCC1", "CCOC(=O)C1CCNCC1", "C#Cc1ccccc1" ], "products": [ "CCOC(=O)C1CCN(C2(C#Cc3ccccc3)CCCCC2)CC1" ] }, "za": { "reactants": [ "C1CC(=O)CCC1", "CC(C)(C)OC(=O)N1CCNCC1", "C#Cc1ccccc1" ], "products": [ "CC(C)(C)OC(=O)N1CCN(C2(C#Cc3ccccc3)CCCCC2)CC1" ] } } }, { "file_name": "ejoc202300810 example 1.png", "reaction_template": { "reactants": [ "[1*]C(=O)/C=C(/C(=O)OCC)C(=O)c1ccccc1", "N#CN" ], "products": [ "[7*]c1oc(-c2ccccc2)c(C(=O)OCC)c1NC(N)=O" ] }, "detailed_reactions": { "a": { "reactants": [ "CCOC(=O)/C(=C/C(=O)c1ccccc1)C(=O)c1ccccc1", "N#CN" ], "products": [ "CCOC(=O)c1c(-c2ccccc2)oc(-c2ccccc2)c1NC(N)=O" ] }, "b": { "reactants": [ "CCOC(=O)/C(=C/C(=O)c1ccc(C)cc1)C(=O)c1ccccc1", "N#CN" ], "products": [ "CCOC(=O)c1c(-c2ccccc2)oc(-c2ccc(C)cc2)c1NC(N)=O" ] }, "c": { "reactants": [ "CCOC(=O)/C(=C/C(=O)c1ccc(OC)cc1)C(=O)c1ccccc1", "N#CN" ], "products": [ "CCOC(=O)c1c(-c2ccccc2)oc(-c2ccc(OC)cc2)c1NC(N)=O" ] }, "d": { "reactants": [ "CCOC(=O)/C(=C/C(=O)c1ccc(F)cc1)C(=O)c1ccccc1", "N#CN" ], "products": [ "CCOC(=O)c1c(-c2ccccc2)oc(-c2ccc(F)cc2)c1NC(N)=O" ] }, "e": { "reactants": [ "CCOC(=O)/C(=C/C(=O)c1ccc(Cl)cc1)C(=O)c1ccccc1", "N#CN" ], "products": [ "CCOC(=O)c1c(-c2ccccc2)oc(-c2ccc(Cl)cc2)c1NC(N)=O" ] }, "f": { "reactants": [ "CCOC(=O)/C(=C/C(=O)c1ccc(Cl)cc1Cl)C(=O)c1ccccc1", "N#CN" ], "products": [ "CCOC(=O)c1c(-c2ccccc2)oc(-c2ccc(Cl)cc2Cl)c1NC(N)=O" ] }, "g": { "reactants": [ "CCOC(=O)/C(=C/C(=O)c1ccc(Cl)c(Cl)c1)C(=O)c1ccccc1", "N#CN" ], "products": [ "CCOC(=O)c1c(-c2ccccc2)oc(-c2ccc(Cl)c(Cl)c2)c1NC(N)=O" ] }, "h": { "reactants": [ "CCOC(=O)/C(=C/C(=O)c1ccc(Br)cc1)C(=O)c1ccccc1", "N#CN" ], "products": [ "CCOC(=O)c1c(-c2ccccc2)oc(-c2ccc(Br)cc2)c1NC(N)=O" ] }, "i": { "reactants": [ "CCOC(=O)/C(=C/C(=O)c1ccc([N+](=O)[O-])cc1)C(=O)c1ccccc1", "N#CN" ], "products": [ "CCOC(=O)c1c(-c2ccccc2)oc(-c2ccc([N+](=O)[O-])cc2)c1NC(N)=O" ] }, "j": { "reactants": [ "CCOC(=O)/C(=C/C(=O)c1ccsc1)C(=O)c1ccccc1", "N#CN" ], "products": [ "CCOC(=O)c1c(-c2ccccc2)oc(-c2ccsc2)c1NC(N)=O" ] }, "k": { "reactants": [ "CCOC(=O)/C(=C/C(=O)c1cc2ccccc2o1)C(=O)c1ccccc1", "N#CN" ], "products": [ "CCOC(=O)c1c(-c2ccccc2)oc(-c2cc3ccccc3o2)c1NC(N)=O" ] }, "l": { "reactants": [ "CCOC(=O)/C(=C/C(=O)c1cccc2ccccc12)C(=O)c1ccccc1", "N#CN" ], "products": [ "CCOC(=O)c1c(-c2ccccc2)oc(-c2cccc3ccccc23)c1NC(N)=O" ] }, "m": { "reactants": [ "CCOC(=O)/C(=C/C(=O)c1ccc2ccccc2c1)C(=O)c1ccccc1", "N#CN" ], "products": [ "CCOC(=O)c1c(-c2ccccc2)oc(-c2ccc3ccccc3c2)c1NC(N)=O" ] } } }, { "file_name": "ejoc202300810 example 2.png", "reaction_template": { "reactants": [ "[2*]C(=O)/C(=C\\C(=O)c1ccccc1)C(=O)OCC", "N#CN" ], "products": [ "[2*]c1oc(-c2ccccc2)c(NC(N)=O)c1C(=O)OCC" ] }, "detailed_reactions": { "n": { "reactants": [ "CCOC(=O)/C(=C/C(=O)c1ccccc1)C(=O)c1cccc(C)c1", "N#CN" ], "products": [ "CCOC(=O)c1c(-c2cccc(C)c2)oc(-c2ccccc2)c1NC(N)=O" ] }, "o": { "reactants": [ "CCOC(=O)/C(=C/C(=O)c1ccccc1)C(=O)c1ccc(C)cc1", "N#CN" ], "products": [ "CCOC(=O)c1c(-c2ccc(C)cc2)oc(-c2ccccc2)c1NC(N)=O" ] }, "p": { "reactants": [ "CCOC(=O)/C(=C/C(=O)c1ccccc1)C(=O)c1ccc(OC)cc1", "N#CN" ], "products": [ "CCOC(=O)c1c(-c2ccc(OC)cc2)oc(-c2ccccc2)c1NC(N)=O" ] }, "q": { "reactants": [ "CCOC(=O)/C(=C/C(=O)c1ccccc1)C(=O)c1cccc(Cl)c1", "N#CN" ], "products": [ "CCOC(=O)c1c(-c2cccc(Cl)c2)oc(-c2ccccc2)c1NC(N)=O" ] }, "r": { "reactants": [ "CCOC(=O)/C(=C/C(=O)c1ccccc1)C(=O)c1ccc(Cl)cc1", "N#CN" ], "products": [ "CCOC(=O)c1c(-c2ccc(Cl)cc2)oc(-c2ccccc2)c1NC(N)=O" ] }, "s": { "reactants": [ "CCOC(=O)/C(=C/C(=O)c1ccccc1)C(=O)c1ccc(Br)cc1", "N#CN" ], "products": [ "CCOC(=O)c1c(-c2ccc(Br)cc2)oc(-c2ccccc2)c1NC(N)=O" ] }, "t": { "reactants": [ "CCOC(=O)/C(=C/C(=O)c1ccccc1)C(=O)c1ccc([N+](=O)[O-])cc1", "N#CN" ], "products": [ "CCOC(=O)c1c(-c2ccc([N+](=O)[O-])cc2)oc(-c2ccccc2)c1NC(N)=O" ] } } }, { "file_name": "ejoc202300810 example 3.png", "reaction_template": { "reactants": [ "[2*]c1oc([7*])c(NC(N)=O)c1C(=O)OCC" ], "products": [ "[2*]c1oc([7*])c2[nH]c(=O)[nH]c(=O)c12" ] }, "detailed_reactions": { "a": { "reactants": [ "CCOC(=O)c1c(-c2ccccc2)oc(-c2ccccc2)c1NC(N)=O" ], "products": [ "O=c1[nH]c(=O)c2c(-c3ccccc3)oc(-c3ccccc3)c2[nH]1" ] }, "b": { "reactants": [ "CCOC(=O)c1c(-c2ccccc2)oc(-c2ccc(C)cc2)c1NC(N)=O" ], "products": [ "Cc1ccc(-c2oc(-c3ccccc3)c3c(=O)[nH]c(=O)[nH]c23)cc1" ] }, "c": { "reactants": [ "CCOC(=O)c1c(-c2ccccc2)oc(-c2ccc(F)cc2)c1NC(N)=O" ], "products": [ "O=c1[nH]c(=O)c2c(-c3ccccc3)oc(-c3ccc(F)cc3)c2[nH]1" ] }, "d": { "reactants": [ "CCOC(=O)c1c(-c2ccccc2)oc(-c2ccc(Cl)cc2)c1NC(N)=O" ], "products": [ "O=c1[nH]c(=O)c2c(-c3ccccc3)oc(-c3ccc(Cl)cc3)c2[nH]1" ] }, "e": { "reactants": [ "CCOC(=O)c1c(-c2ccccc2)oc(-c2ccc(Br)cc2)c1NC(N)=O" ], "products": [ "O=c1[nH]c(=O)c2c(-c3ccccc3)oc(-c3ccc(Br)cc3)c2[nH]1" ] }, "f": { "reactants": [ "CCOC(=O)c1c(-c2cccc(C)c2)oc(-c2ccccc2)c1NC(N)=O" ], "products": [ "Cc1cccc(-c2oc(-c3ccccc3)c3[nH]c(=O)[nH]c(=O)c23)c1" ] }, "g": { "reactants": [ "CCOC(=O)c1c(-c2ccc(OC)cc2)oc(-c2ccccc2)c1NC(N)=O" ], "products": [ "COc1ccc(-c2oc(-c3ccccc3)c3[nH]c(=O)[nH]c(=O)c23)cc1" ] }, "h": { "reactants": [ "CCOC(=O)c1c(-c2cccc(Cl)c2)oc(-c2ccccc2)c1NC(N)=O" ], "products": [ "O=c1[nH]c(=O)c2c(-c3cccc(Cl)c3)oc(-c3ccccc3)c2[nH]1" ] }, "i": { "reactants": [ "CCOC(=O)c1c(-c2ccc(Cl)cc2)oc(-c2ccccc2)c1NC(N)=O" ], "products": [ "O=c1[nH]c(=O)c2c(-c3ccc(Cl)cc3)oc(-c3ccccc3)c2[nH]1" ] } } }, { "file_name": "ejoc202300829 example 1.png", "reaction_template": { "reactants": [ "*c1cn2ccccc2n1" ], "products": [ "*c1nc2ccccn2c1C=O" ] }, "detailed_reactions": { "b": { "reactants": [ "Cc1ccc(-c2cn3ccccc3n2)cc1" ], "products": [ "Cc1ccc(-c2nc3ccccn3c2C=O)cc1" ] }, "c": { "reactants": [ "COc1ccc(-c2cn3ccccc3n2)cc1" ], "products": [ "COc1ccc(-c2nc3ccccn3c2C=O)cc1" ] }, "d": { "reactants": [ "Fc1ccc(-c2cn3ccccc3n2)cc1" ], "products": [ "O=Cc1c(-c2ccc(F)cc2)nc2ccccn12" ] }, "e": { "reactants": [ "Clc1ccc(-c2cn3ccccc3n2)cc1" ], "products": [ "O=Cc1c(-c2ccc(Cl)cc2)nc2ccccn12" ] }, "f": { "reactants": [ "N#Cc1ccc(-c2cn3ccccc3n2)cc1" ], "products": [ "N#Cc1ccc(-c2nc3ccccn3c2C=O)cc1" ] }, "g": { "reactants": [ "CC(=O)Oc1ccc(-c2cn3ccccc3n2)cc1" ], "products": [ "CC(=O)Oc1ccc(-c2nc3ccccn3c2C=O)cc1" ] }, "h": { "reactants": [ "c1ccc2cc(-c3cn4ccccc4n3)ccc2c1" ], "products": [ "O=Cc1c(-c2ccc3ccccc3c2)nc2ccccn12" ] }, "i": { "reactants": [ "c1csc(-c2cn3ccccc3n2)c1" ], "products": [ "O=Cc1c(-c2cccs2)nc2ccccn12" ] } } }, { "file_name": "ejoc202300802 example 1.png", "reaction_template": { "reactants": [ "*C(C#C)OC(=O)C", "[H]P(=O)(c1ccccc1)c1ccccc1O" ], "products": [ "*CC1=CP(=O)(c2ccccc2)c2ccccc2O1" ] }, "detailed_reactions": { "aa": { "reactants": [ "C#CC(OC(=O)C)c1ccccc1", "O=[PH](c1ccccc1)c1ccccc1O" ], "products": [ "O=P1(c2ccccc2)C=C(Cc2ccccc2)Oc2ccccc21" ] }, "ba": { "reactants": [ "C#CC(OC(=O)C)c1ccc(F)cc1", "O=[PH](c1ccccc1)c1ccccc1O" ], "products": [ "O=P1(c2ccccc2)C=C(Cc2ccc(F)cc2)Oc2ccccc21" ] }, "ca": { "reactants": [ "C#CC(OC(=O)C)c1ccc(Cl)cc1", "O=[PH](c1ccccc1)c1ccccc1O" ], "products": [ "O=P1(c2ccccc2)C=C(Cc2ccc(Cl)cc2)Oc2ccccc21" ] }, "da": { "reactants": [ "C#CC(OC(=O)C)c1ccc(Br)cc1", "O=[PH](c1ccccc1)c1ccccc1O" ], "products": [ "O=P1(c2ccccc2)C=C(Cc2ccc(Br)cc2)Oc2ccccc21" ] }, "ea": { "reactants": [ "C#CC(OC(=O)C)c1ccc(C)cc1", "O=[PH](c1ccccc1)c1ccccc1O" ], "products": [ "O=P1(c2ccccc2)C=C(Cc2ccc(C)cc2)Oc2ccccc21" ] }, "fa": { "reactants": [ "C#CC(OC(=O)C)c1ccc(OC)cc1", "O=[PH](c1ccccc1)c1ccccc1O" ], "products": [ "O=P1(c2ccccc2)C=C(Cc2ccc(OC)cc2)Oc2ccccc21" ] }, "ga": { "reactants": [ "C#CC(OC(=O)C)c1cccc(Cl)c1", "O=[PH](c1ccccc1)c1ccccc1O" ], "products": [ "O=P1(c2ccccc2)C=C(Cc2cccc(Cl)c2)Oc2ccccc21" ] }, "ha": { "reactants": [ "C#CC(OC(=O)C)c1cccc(Br)c1", "O=[PH](c1ccccc1)c1ccccc1O" ], "products": [ "O=P1(c2ccccc2)C=C(Cc2cccc(Br)c2)Oc2ccccc21" ] }, "ia": { "reactants": [ "C#CC(OC(=O)C)c1cccc(C)c1", "O=[PH](c1ccccc1)c1ccccc1O" ], "products": [ "Cc1cccc(CC2=CP(=O)(c3ccccc3)c3ccccc3O2)c1" ] }, "ja": { "reactants": [ "C#CC(OC(=O)C)c1ccccc1Cl", "O=[PH](c1ccccc1)c1ccccc1O" ], "products": [ "O=P1(c2ccccc2)C=C(Cc2ccccc2Cl)Oc2ccccc21" ] }, "ka": { "reactants": [ "C#CC(OC(=O)C)c1ccccc1Br", "O=[PH](c1ccccc1)c1ccccc1O" ], "products": [ "O=P1(c2ccccc2)C=C(Cc2ccccc2Br)Oc2ccccc21" ] }, "la": { "reactants": [ "C#CC(OC(=O)C)c1ccccc1C", "O=[PH](c1ccccc1)c1ccccc1O" ], "products": [ "Cc1ccccc1CC1=CP(=O)(c2ccccc2)c2ccccc2O1" ] }, "ma": { "reactants": [ "C#CC(OC(=O)C)c1ccc2ccccc2c1", "O=[PH](c1ccccc1)c1ccccc1O" ], "products": [ "O=P1(c2ccccc2)C=C(Cc2ccc3ccccc3c2)Oc2ccccc21" ] }, "na": { "reactants": [ "C#CC(OC(=O)C)c1csc2ccccc12", "O=[PH](c1ccccc1)c1ccccc1O" ], "products": [ "O=P1(c2ccccc2)C=C(Cc2csc3ccccc23)Oc2ccccc21" ] }, "oa": { "reactants": [ "C#CC(OC(=O)C)c1ccco1", "O=[PH](c1ccccc1)c1ccccc1O" ], "products": [ "O=P1(c2ccccc2)C=C(Cc2ccco2)Oc2ccccc21" ] } } }, { "file_name": "anie.202313838 example 1.png", "reaction_template": { "reactants": [ "[1*]/C=C/C(F)F", "CC(C)C=NC(C)C(=O)OC(C)(C)C" ], "products": [ "[1*]/C=C/C(F)C(C)(N)C(=O)OC(C)(C)C" ] }, "detailed_reactions": { "ab": { "reactants": [ "Fc1ccc(C=CC(F)F)cc1", "CC(C)C=NC(C)C(=O)OC(C)(C)C" ], "products": [ "CC(C)(C)OC(=O)[C@](C)(N)C(F)/C=C/c1ccc(F)cc1" ] }, "ac": { "reactants": [ "FC(F)C=Cc1ccc(Cl)cc1", "CC(C)C=NC(C)C(=O)OC(C)(C)C" ], "products": [ "CC(C)(C)OC(=O)[C@](C)(N)C(F)/C=C/c1ccc(Cl)cc1" ] }, "ad": { "reactants": [ "FC(F)C=Cc1ccc(Br)cc1", "CC(C)C=NC(C)C(=O)OC(C)(C)C" ], "products": [ "CC(C)(C)OC(=O)[C@](C)(N)C(F)/C=C/c1ccc(Br)cc1" ] }, "ae": { "reactants": [ "FC(F)C=Cc1cc(Br)cc(Br)c1", "CC(C)C=NC(C)C(=O)OC(C)(C)C" ], "products": [ "CC(C)(C)OC(=O)[C@](C)(N)C(F)/C=C/c1cc(Br)cc(Br)c1" ] }, "af": { "reactants": [ "FC(F)C=Cc1ccc(C(F)(F)F)cc1", "CC(C)C=NC(C)C(=O)OC(C)(C)C" ], "products": [ "CC(C)(C)OC(=O)[C@](C)(N)C(F)/C=C/c1ccc(C(F)(F)F)cc1" ] }, "ag": { "reactants": [ "Fc1cccc(C=CC(F)F)c1", "CC(C)C=NC(C)C(=O)OC(C)(C)C" ], "products": [ "CC(C)(C)OC(=O)[C@](C)(N)C(F)/C=C/c1cccc(F)c1" ] }, "ah": { "reactants": [ "FC(F)C=Cc1cccc(Cl)c1", "CC(C)C=NC(C)C(=O)OC(C)(C)C" ], "products": [ "CC(C)(C)OC(=O)[C@](C)(N)C(F)/C=C/c1cccc(Cl)c1" ] }, "ai": { "reactants": [ "FC(F)C=Cc1cccc(C(F)(F)F)c1", "CC(C)C=NC(C)C(=O)OC(C)(C)C" ], "products": [ "CC(C)(C)OC(=O)[C@](C)(N)C(F)/C=C/c1cccc(C(F)(F)F)c1" ] }, "aj": { "reactants": [ "Cc1cccc(C=CC(F)F)c1", "CC(C)C=NC(C)C(=O)OC(C)(C)C" ], "products": [ "Cc1cccc(/C=C/[C@@H](F)[C@](C)(N)C(=O)OC(C)(C)C)c1" ] }, "ak": { "reactants": [ "COc1cccc(C=CC(F)F)c1", "CC(C)C=NC(C)C(=O)OC(C)(C)C" ], "products": [ "COc1cccc(/C=C/C(F)[C@@](C)(N)C(=O)OC(C)(C)C)c1" ] }, "al": { "reactants": [ "Fc1ccccc1C=CC(F)F", "CC(C)C=NC(C)C(=O)OC(C)(C)C" ], "products": [ "CC(C)(C)OC(=O)[C@](C)(N)C(F)/C=C/c1ccccc1F" ] }, "am": { "reactants": [ "c1cc2ccccc2cc1C=CC(F)F", "CC(C)C=NC(C)C(=O)OC(C)(C)C" ], "products": [ "CC(C)(C)OC(=O)[C@](C)(N)C(F)/C=C/c1ccc2ccccc2c1" ] } } }, { "file_name": "ejoc.202300707 example 1.png", "reaction_template": { "reactants": [ "c1ccc2[nH]ccc2c1", "*O" ], "products": [ "*c1c[nH]c2ccccc12" ] }, "detailed_reactions": { "a": { "reactants": [ "c1ccc2[nH]ccc2c1", "OCc1ccccc1" ], "products": [ "c1ccc(Cc2c[nH]c3ccccc23)cc1" ] }, "b": { "reactants": [ "c1ccc2[nH]ccc2c1", "CCCCCO" ], "products": [ "CCCCCc1c[nH]c2ccccc12" ] }, "c": { "reactants": [ "c1ccc2[nH]ccc2c1", "CCCCCCCCO" ], "products": [ "CCCCCCCCc1c[nH]c2ccccc12" ] }, "d": { "reactants": [ "c1ccc2[nH]ccc2c1", "C/C=C/CCCO" ], "products": [ "C/C=C/CCCc1c[nH]c2ccccc12" ] }, "e": { "reactants": [ "c1ccc2[nH]ccc2c1", "COCCO" ], "products": [ "COCCc1c[nH]c2ccccc12" ] }, "f": { "reactants": [ "c1ccc2[nH]ccc2c1", "COc1ccc(CO)cc1" ], "products": [ "COc1ccc(Cc2c[nH]c3ccccc23)cc1" ] }, "g": { "reactants": [ "c1ccc2[nH]ccc2c1", "OCc1ccncc1" ], "products": [ "c1ccc2c(Cc3ccncc3)c[nH]c2c1" ] }, "h": { "reactants": [ "c1ccc2[nH]ccc2c1", "OCc1ccco1" ], "products": [ "c1coc(Cc2c[nH]c3ccccc23)c1" ] }, "i": { "reactants": [ "c1ccc2[nH]ccc2c1", "CC(C)=CCC[C@H](C)CCO" ], "products": [ "CC(C)=CCC[C@H](C)CCc1c[nH]c2ccccc12" ] } } }, { "file_name": "ejoc.202300707 example 2.png", "reaction_template": { "reactants": [ "CC(=O)c1ccccc1", "*O" ], "products": [ "*CC(=O)c1ccccc1" ] }, "detailed_reactions": { "a": { "reactants": [ "CC(=O)c1ccccc1", "OCc1ccccc1" ], "products": [ "O=C(CCc1ccccc1)c1ccccc1" ] }, "b": { "reactants": [ "CC(=O)c1ccccc1", "CCCCCO" ], "products": [ "CCCCCCC(=O)c1ccccc1" ] }, "c": { "reactants": [ "CC(=O)c1ccccc1", "CCCCCCCCO" ], "products": [ "CCCCCCCCCC(=O)c1ccccc1" ] }, "d": { "reactants": [ "CC(=O)c1ccccc1", "C/C=C/CCCO" ], "products": [ "C/C=C/CCCCC(=O)c1ccccc1" ] }, "e": { "reactants": [ "CC(=O)c1ccccc1", "COCCO" ], "products": [ "COCCCC(=O)c1ccccc1" ] }, "f": { "reactants": [ "CC(=O)c1ccccc1", "COc1ccc(CO)cc1" ], "products": [ "COc1ccc(CCC(=O)c2ccccc2)cc1" ] }, "g": { "reactants": [ "CC(=O)c1ccccc1", "OCc1ccncc1" ], "products": [ "O=C(CCc1ccncc1)c1ccccc1" ] }, "h": { "reactants": [ "CC(=O)c1ccccc1", "OCc1ccco1" ], "products": [ "O=C(CCc1ccco1)c1ccccc1" ] }, "i": { "reactants": [ "CC(=O)c1ccccc1", "CC(C)=CCC[C@H](C)CCO" ], "products": [ "CC(C)=CCC[C@H](C)CCCC(=O)c1ccccc1" ] }, "j": { "reactants": [ "CC(=O)c1ccccc1", "OCCc1ccccc1" ], "products": [ "O=C(CCCc1ccccc1)c1ccccc1" ] }, "k": { "reactants": [ "CC(=O)c1ccccc1", "CC1(C)[C@H]2CC[C@@H](CO)[C@@H]1C2" ], "products": [ "CC1(C)[C@H]2CC[C@@H](CCC(=O)c3ccccc3)[C@@H]1C2" ] }, "l": { "reactants": [ "CC(=O)c1ccccc1", "OCC1CC2C=CC1C2" ], "products": [ "O=C(CCC1CC2C=CC1C2)c1ccccc1" ] }, "m": { "reactants": [ "CC(=O)c1ccccc1", "CC(CO)c1ccccc1" ], "products": [ "CC(CCC(=O)c1ccccc1)c1ccccc1" ] }, "n": { "reactants": [ "CC(=O)c1ccccc1", "OC1CCCCC1" ], "products": [ "O=C(CC1CCCCC1)c1ccccc1" ] } } }, { "file_name": "ejoc.202300733 example 1.png", "reaction_template": { "reactants": [ "Nc1ccccc1SSc1ccccc1N", "*C#CBr" ], "products": [ "*C#CSc1ccccc1N" ] }, "detailed_reactions": { "a": { "reactants": [ "Nc1ccccc1SSc1ccccc1N", "BrC#Cc1ccccc1" ], "products": [ "Nc1ccccc1SC#Cc1ccccc1" ] }, "b": { "reactants": [ "Nc1ccccc1SSc1ccccc1N", "COc1ccc(C#CBr)cc1" ], "products": [ "COc1ccc(C#CSc2ccccc2N)cc1" ] }, "c": { "reactants": [ "Nc1ccccc1SSc1ccccc1N", "Cc1ccc(C#CBr)cc1" ], "products": [ "Cc1ccc(C#CSc2ccccc2N)cc1" ] }, "d": { "reactants": [ "Nc1ccccc1SSc1ccccc1N", "CC(C)(C)c1ccc(C#CBr)cc1" ], "products": [ "CC(C)(C)c1ccc(C#CSc2ccccc2N)cc1" ] }, "e": { "reactants": [ "Nc1ccccc1SSc1ccccc1N", "Fc1ccc(C#CBr)cc1" ], "products": [ "Nc1ccccc1SC#Cc1ccc(F)cc1" ] }, "f": { "reactants": [ "Nc1ccccc1SSc1ccccc1N", "Clc1ccc(C#CBr)cc1" ], "products": [ "Nc1ccccc1SC#Cc1ccc(Cl)cc1" ] }, "g": { "reactants": [ "Nc1ccccc1SSc1ccccc1N", "BrC#Cc1ccc(Br)cc1" ], "products": [ "Nc1ccccc1SC#Cc1ccc(Br)cc1" ] }, "h": { "reactants": [ "Nc1ccccc1SSc1ccccc1N", "N#Cc1ccc(C#CBr)cc1" ], "products": [ "N#Cc1ccc(C#CSc2ccccc2N)cc1" ] }, "i": { "reactants": [ "Nc1ccccc1SSc1ccccc1N", "O=[N+]([O-])c1ccc(C#CBr)cc1" ], "products": [ "Nc1ccccc1SC#Cc1ccc([N+](=O)[O-])cc1" ] }, "j": { "reactants": [ "Nc1ccccc1SSc1ccccc1N", "BrC#Cc1cccs1" ], "products": [ "Nc1ccccc1SC#Cc1cccs1" ] }, "k": { "reactants": [ "Nc1ccccc1SSc1ccccc1N", "CCCCCC#CBr" ], "products": [ "CCCCCC#CSc1ccccc1N" ] }, "l": { "reactants": [ "Nc1ccccc1SSc1ccccc1N", "CCCC#CBr" ], "products": [ "CCCC#CSc1ccccc1N" ] } } }, { "file_name": "ejoc.202300733 example 2.png", "reaction_template": { "reactants": [ "*I", "CSC#C[Si](C)(C)C" ], "products": [ "*C#CSC" ] }, "detailed_reactions": { "a": { "reactants": [ "Ic1ccccc1", "CSC#C[Si](C)(C)C" ], "products": [ "CSC#Cc1ccccc1" ] }, "b": { "reactants": [ "COc1ccc(I)cc1", "CSC#C[Si](C)(C)C" ], "products": [ "COc1ccc(C#CSC)cc1" ] }, "c": { "reactants": [ "COc1ccccc1I", "CSC#C[Si](C)(C)C" ], "products": [ "COc1ccccc1C#CSC" ] }, "d": { "reactants": [ "Cc1ccc(I)cc1", "CSC#C[Si](C)(C)C" ], "products": [ "CSC#Cc1ccc(C)cc1" ] }, "e": { "reactants": [ "Cc1ccccc1I", "CSC#C[Si](C)(C)C" ], "products": [ "CSC#Cc1ccccc1C" ] }, "f": { "reactants": [ "Brc1ccc(I)cc1", "CSC#C[Si](C)(C)C" ], "products": [ "CSC#Cc1ccc(Br)cc1" ] }, "g": { "reactants": [ "Clc1ccc(I)cc1", "CSC#C[Si](C)(C)C" ], "products": [ "CSC#Cc1ccc(Cl)cc1" ] }, "h": { "reactants": [ "Clc1ccccc1I", "CSC#C[Si](C)(C)C" ], "products": [ "CSC#Cc1ccccc1Cl" ] }, "i": { "reactants": [ "FC(F)(F)c1ccc(I)cc1", "CSC#C[Si](C)(C)C" ], "products": [ "CSC#Cc1ccc(C(F)(F)F)cc1" ] }, "j": { "reactants": [ "FC(F)(F)c1ccccc1I", "CSC#C[Si](C)(C)C" ], "products": [ "CSC#Cc1ccccc1C(F)(F)F" ] }, "k": { "reactants": [ "N#Cc1ccc(I)cc1", "CSC#C[Si](C)(C)C" ], "products": [ "CSC#Cc1ccc(C#N)cc1" ] }, "l": { "reactants": [ "N#Cc1ccccc1I", "CSC#C[Si](C)(C)C" ], "products": [ "CSC#Cc1ccccc1C#N" ] }, "m": { "reactants": [ "O=[N+]([O-])c1ccc(I)cc1", "CSC#C[Si](C)(C)C" ], "products": [ "CSC#Cc1ccc([N+](=O)[O-])cc1" ] }, "n": { "reactants": [ "O=[N+]([O-])c1ccccc1I", "CSC#C[Si](C)(C)C" ], "products": [ "CSC#Cc1ccccc1[N+](=O)[O-]" ] }, "o": { "reactants": [ "Ic1cccc2ccccc12", "CSC#C[Si](C)(C)C" ], "products": [ "CSC#Cc1cccc2ccccc12" ] }, "p": { "reactants": [ "Ic1ccncc1", "CSC#C[Si](C)(C)C" ], "products": [ "CSC#Cc1ccncc1" ] }, "q": { "reactants": [ "Ic1cnccc1", "CSC#C[Si](C)(C)C" ], "products": [ "CSC#Cc1cnccc1" ] }, "r": { "reactants": [ "Ic1ccccn1", "CSC#C[Si](C)(C)C" ], "products": [ "CSC#Cc1ccccn1" ] }, "s": { "reactants": [ "Ic1ccsc1", "CSC#C[Si](C)(C)C" ], "products": [ "CSC#Cc1ccsc1" ] }, "t": { "reactants": [ "Ic1cccs1", "CSC#C[Si](C)(C)C" ], "products": [ "CSC#Cc1cccs1" ] } } }, { "file_name": "ejoc.202300733 example 3.png", "reaction_template": { "reactants": [ "*S(=O)CCC(=O)OC", "[1*]C#C[H]" ], "products": [ "*SC#C[1*]" ] }, "detailed_reactions": { "a": { "reactants": [ "COC(=O)CCS(=O)c1ccc(C)cc1", "C#Cc1ccc(C)cc1" ], "products": [ "Cc1ccc(C#CSc2ccc(C)cc2)cc1" ] }, "b": { "reactants": [ "COC(=O)CCS(=O)c1ccc(C)cc1", "C#Cc1ccc(Cl)cc1" ], "products": [ "Cc1ccc(SC#Cc2ccc(Cl)cc2)cc1" ] }, "c": { "reactants": [ "COC(=O)CCS(=O)c1ccc(C)cc1", "C#Cc1ccc(Br)cc1" ], "products": [ "Cc1ccc(SC#Cc2ccc(Br)cc2)cc1" ] }, "d": { "reactants": [ "COC(=O)CCS(=O)c1ccc(C)cc1", "C#Cc1ccc(F)cc1" ], "products": [ "Cc1ccc(SC#Cc2ccc(F)cc2)cc1" ] }, "e": { "reactants": [ "COC(=O)CCS(=O)c1ccc(C)cc1", "C#Cc1ccc(OC)cc1" ], "products": [ "COc1ccc(C#CSc2ccc(C)cc2)cc1" ] }, "f": { "reactants": [ "COC(=O)CCS(=O)c1ccc(C)cc1", "C#Cc1ccc([N+](=O)[O-])cc1" ], "products": [ "Cc1ccc(SC#Cc2ccc([N+](=O)[O-])cc2)cc1" ] }, "g": { "reactants": [ "COC(=O)CCS(=O)c1ccc(C)cc1", "C#Cc1ccc(C=O)cc1" ], "products": [ "Cc1ccc(SC#Cc2ccc(C=O)cc2)cc1" ] }, "h": { "reactants": [ "COC(=O)CCS(=O)c1ccc(C)cc1", "C#Cc1cccc(N)c1" ], "products": [ "Cc1ccc(SC#Cc2cccc(N)c2)cc1" ] }, "i": { "reactants": [ "COC(=O)CCS(=O)c1ccc(C)cc1", "C#CCCCC" ], "products": [ "Cc1ccc(SC#CCCCC)cc1" ] }, "j": { "reactants": [ "COC(=O)CCS(=O)c1ccccc1C", "C#Cc1ccccc1" ], "products": [ "Cc1ccccc1SC#Cc1ccccc1" ] }, "k": { "reactants": [ "COC(=O)CCS(=O)c1cccc(C)c1", "C#Cc1ccccc1" ], "products": [ "Cc1cccc(SC#Cc2ccccc2)c1" ] }, "l": { "reactants": [ "COC(=O)CCS(=O)c1ccc(C)cc1", "C#Cc1ccccc1" ], "products": [ "Cc1ccc(SC#Cc2ccccc2)cc1" ] }, "m": { "reactants": [ "COC(=O)CCS(=O)c1ccc(F)cc1", "C#Cc1ccccc1" ], "products": [ "Fc1ccc(SC#Cc2ccccc2)cc1" ] }, "n": { "reactants": [ "COC(=O)CCS(=O)c1ccc(Cl)cc1", "C#Cc1ccccc1" ], "products": [ "Clc1ccc(SC#Cc2ccccc2)cc1" ] }, "o": { "reactants": [ "COC(=O)CCS(=O)c1ccc(Br)cc1", "C#Cc1ccccc1" ], "products": [ "Brc1ccc(SC#Cc2ccccc2)cc1" ] }, "p": { "reactants": [ "COC(=O)CCS(=O)c1ccc([N+](=O)[O-])cc1", "C#Cc1ccccc1" ], "products": [ "O=[N+]([O-])c1ccc(SC#Cc2ccccc2)cc1" ] }, "q": { "reactants": [ "CCCCS(=O)CCC(=O)OC", "C#Cc1ccccc1" ], "products": [ "CCCCSC#Cc1ccccc1" ] }, "r": { "reactants": [ "COC(=O)CCS(=O)CCC(=O)OC", "C#Cc1ccccc1" ], "products": [ "COC(=O)CCSC#Cc1ccccc1" ] } } }, { "file_name": "ejoc.202300733 example 4.png", "reaction_template": { "reactants": [ "CSS(=O)(=O)[O-].[Na+]", "*C#C" ], "products": [ "*C#CSC" ] }, "detailed_reactions": { "9a": { "reactants": [ "CSS(=O)(=O)[O-].[Na+]", "C#Cc1ccccc1" ], "products": [ "CSC#Cc1ccccc1" ] }, "9b": { "reactants": [ "CSS(=O)(=O)[O-].[Na+]", "C#Cc1ccc(OC)cc1" ], "products": [ "COc1ccc(C#CSC)cc1" ] }, "9d": { "reactants": [ "CSS(=O)(=O)[O-].[Na+]", "C#Cc1ccc(C)cc1" ], "products": [ "Cc1ccc(C#CSC)cc1" ] }, "9f": { "reactants": [ "CSS(=O)(=O)[O-].[Na+]", "C#Cc1ccc(Br)cc1" ], "products": [ "CSC#Cc1ccc(Br)cc1" ] }, "9g": { "reactants": [ "CSS(=O)(=O)[O-].[Na+]", "C#Cc1ccc(Cl)cc1" ], "products": [ "CSC#Cc1ccc(Cl)cc1" ] }, "9i": { "reactants": [ "CSS(=O)(=O)[O-].[Na+]", "C#Cc1ccc(C(F)(F)F)cc1" ], "products": [ "CSC#Cc1ccc(C(F)(F)F)cc1" ] }, "9m": { "reactants": [ "CSS(=O)(=O)[O-].[Na+]", "C#Cc1ccc([N+](=O)[O-])cc1" ], "products": [ "CSC#Cc1ccc([N+](=O)[O-])cc1" ] }, "18a": { "reactants": [ "CSS(=O)(=O)[O-].[Na+]", "C#Cc1ccc(CCCCC)cc1" ], "products": [ "CSC#Cc1ccc(CCCCC)cc1" ] }, "18b": { "reactants": [ "CSS(=O)(=O)[O-].[Na+]", "C#Cc1ccc(C#N)cc1" ], "products": [ "N#Cc1ccc(C#CSC)cc1" ] }, "18c": { "reactants": [ "CSS(=O)(=O)[O-].[Na+]", "C#Cc1ccc(C(=O)C)cc1" ], "products": [ "CC(=O)c1ccc(C#CSC)cc1" ] }, "18d": { "reactants": [ "CSS(=O)(=O)[O-].[Na+]", "C#Cc1cc(F)ccc1" ], "products": [ "CSC#Cc1cc(F)ccc1" ] }, "18e": { "reactants": [ "CSS(=O)(=O)[O-].[Na+]", "C#Cc1cc(C#SC)ccc1" ], "products": [ "CSC#Cc1cc(C#CSC)ccc1" ] }, "18f": { "reactants": [ "CSS(=O)(=O)[O-].[Na+]", "C#Cc1c(C)cccc1" ], "products": [ "CSC#Cc1c(C)cccc1" ] }, "18g": { "reactants": [ "CSS(=O)(=O)[O-].[Na+]", "COc1ccc2cc(C#C)ccc2c1" ], "products": [ "COc1ccc2cc(C#CSC)ccc2c1" ] }, "18h": { "reactants": [ "CSS(=O)(=O)[O-].[Na+]", "C#Cc1cccs1" ], "products": [ "CSC#Cc1cccs1" ] }, "18i": { "reactants": [ "CSS(=O)(=O)[O-].[Na+]", "C#CCOc1ccccc1" ], "products": [ "CSC#CCOc1ccccc1" ] } } }, { "file_name": "ejoc.202300733 example 5.png", "reaction_template": { "reactants": [ "*C#C", "[P+](c1ccccc1)(c1ccccc1)c1ccccc1.FC(F)C(=O)[O-]", "S1SSSSSSS1", "[K+].[F-]" ], "products": [ "*C#CSC(F)(F)F" ] }, "detailed_reactions": { "31b": { "reactants": [ "COc1ccc(C#C)cc1", "[P+](c1ccccc1)(c1ccccc1)c1ccccc1.FC(F)C(=O)[O-]", "S1SSSSSSS1", "[K+].[F-]" ], "products": [ "COc1ccc(C#CSC(F)(F)F)cc1" ] }, "33a": { "reactants": [ "C#Cc1ccc(-c2ccccc2)cc1", "[P+](c1ccccc1)(c1ccccc1)c1ccccc1.FC(F)C(=O)[O-]", "S1SSSSSSS1", "[K+].[F-]" ], "products": [ "FC(F)(F)SC#Cc1ccc(-c2ccccc2)cc1" ] }, "33b": { "reactants": [ "CN(C)c1ccc(C#C)cc1", "[P+](c1ccccc1)(c1ccccc1)c1ccccc1.FC(F)C(=O)[O-]", "S1SSSSSSS1", "[K+].[F-]" ], "products": [ "CN(C)c1ccc(C#CSC(F)(F)F)cc1" ] }, "33c": { "reactants": [ "COc1ccc2cc(C#C)ccc2c1", "[P+](c1ccccc1)(c1ccccc1)c1ccccc1.FC(F)C(=O)[O-]", "S1SSSSSSS1", "[K+].[F-]" ], "products": [ "COc1ccc2cc(C#CSC(F)(F)F)ccc2c1" ] }, "33d": { "reactants": [ "C#Cc1cc2ccc3cccc4ccc(c1)c2c34", "[P+](c1ccccc1)(c1ccccc1)c1ccccc1.FC(F)C(=O)[O-]", "S1SSSSSSS1", "[K+].[F-]" ], "products": [ "FC(F)(F)SC#Cc1cc2ccc3cccc4ccc(c1)c2c34" ] }, "33e": { "reactants": [ "C#Cc1ccc2c(c1)Cc1ccccc1-2", "[P+](c1ccccc1)(c1ccccc1)c1ccccc1.FC(F)C(=O)[O-]", "S1SSSSSSS1", "[K+].[F-]" ], "products": [ "FC(F)(F)SC#Cc1ccc2c(c1)Cc1ccccc1-2" ] }, "33f": { "reactants": [ "C#Cc1cnc2ccccc2c1", "[P+](c1ccccc1)(c1ccccc1)c1ccccc1.FC(F)C(=O)[O-]", "S1SSSSSSS1", "[K+].[F-]" ], "products": [ "FC(F)(F)SC#Cc1cnc2ccccc2c1" ] }, "33g": { "reactants": [ "COc1ccc(CN(C)CC#C)cc1", "[P+](c1ccccc1)(c1ccccc1)c1ccccc1.FC(F)C(=O)[O-]", "S1SSSSSSS1", "[K+].[F-]" ], "products": [ "COc1ccc(CN(C)CC#CSC(F)(F)F)cc1" ] } } }, { "file_name": "ejoc.202300733 example 6.png", "reaction_template": { "reactants": [ "*C#CBr", "[Ag+].[S-]C(F)(F)F" ], "products": [ "*C#CSC(F)(F)F" ] }, "detailed_reactions": { "31d": { "reactants": [ "Brc1ccc(C#CBr)cc1", "[Ag+].[S-]C(F)(F)F" ], "products": [ "Brc1ccc(C#CSC(F)(F)F)cc1" ] }, "33a": { "reactants": [ "c1ccccc1-c1ccc(C#CBr)cc1", "[Ag+].[S-]C(F)(F)F" ], "products": [ "c1ccccc1-c1ccc(C#CSC(F)(F)F)cc1" ] }, "35c": { "reactants": [ "Clc1ccc(C#CBr)cc1", "[Ag+].[S-]C(F)(F)F" ], "products": [ "FC(F)(F)SC#Cc1ccc(Cl)cc1" ] }, "35a": { "reactants": [ "BrC#Cc1ccccc1", "[Ag+].[S-]C(F)(F)F" ], "products": [ "FC(F)(F)SC#Cc1ccccc1" ] }, "35b": { "reactants": [ "Fc1ccc(C#CBr)cc1", "[Ag+].[S-]C(F)(F)F" ], "products": [ "Fc1ccc(C#CSC(F)(F)F)cc1" ] }, "35d": { "reactants": [ "COC(OC)c1ccc(C#CBr)cc1", "[Ag+].[S-]C(F)(F)F" ], "products": [ "COC(OC)c1ccc(C#CSC(F)(F)F)cc1" ] }, "35e": { "reactants": [ "N#Cc1ccc(C#CBr)cc1", "[Ag+].[S-]C(F)(F)F" ], "products": [ "N#Cc1ccc(C#CSC(F)(F)F)cc1" ] }, "35f": { "reactants": [ "O=[N+]([O-])c1ccc(C#CBr)cc1", "[Ag+].[S-]C(F)(F)F" ], "products": [ "O=[N+]([O-])c1ccc(C#CSC(F)(F)F)cc1" ] } } }, { "file_name": "ejoc.202300535 example 1.png", "reaction_template": { "reactants": [ "*NC(=O)C(*)=C" ], "products": [ "*NC(=O)[C@](*)(O)CS(=O)(=O)c1ccc(C)cc1" ] }, "detailed_reactions": { "a": { "reactants": [ "C=C(C)C(=O)Nc1ccccc1" ], "products": [ "Cc1ccc(S(=O)(=O)C[C@](C)(O)C(=O)Nc2ccccc2)cc1" ] }, "b": { "reactants": [ "C=C(C)C(=O)Nc1ccc(C)cc1" ], "products": [ "Cc1ccc(NC(=O)[C@](C)(O)CS(=O)(=O)c2ccc(C)cc2)cc1" ] }, "c": { "reactants": [ "C=C(C)C(=O)Nc1ccc(OCC)cc1" ], "products": [ "CCOc1ccc(NC(=O)[C@](C)(O)CS(=O)(=O)c2ccc(C)cc2)cc1" ] }, "d": { "reactants": [ "C=C(C)C(=O)Nc1ccc(C(F)(F)F)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)C[C@@](C)(O)C(=O)Nc2ccc(C(F)(F)F)cc2)cc1" ] }, "e": { "reactants": [ "C=C(C)C(=O)Nc1ccc(Br)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)C[C@](C)(O)C(=O)Nc2ccc(Br)cc2)cc1" ] }, "f": { "reactants": [ "C=C(C)C(=O)Nc1cccc(Br)c1" ], "products": [ "Cc1ccc(S(=O)(=O)C[C@](C)(O)C(=O)Nc2cccc(Br)c2)cc1" ] }, "g": { "reactants": [ "C=C(C)C(=O)Nc1ccccc1C" ], "products": [ "Cc1ccc(S(=O)(=O)C[C@@](C)(O)C(=O)Nc2ccccc2C)cc1" ] }, "h": { "reactants": [ "C=C(C)C(=O)Nc1ccccc1OC" ], "products": [ "COc1ccccc1NC(=O)[C@@](C)(O)CS(=O)(=O)c1ccc(C)cc1" ] }, "i": { "reactants": [ "C=C(C)C(=O)Nc1cc(C)cc(C)c1" ], "products": [ "Cc1ccc(S(=O)(=O)C[C@@](C)(O)C(=O)Nc2cc(C)cc(C)c2)cc1" ] }, "j": { "reactants": [ "C=C(C)C(=O)Nc1ccc(C#N)c(C(F)(F)F)c1" ], "products": [ "Cc1ccc(S(=O)(=O)C[C@@](C)(O)C(=O)Nc2ccc(C#N)c(C(F)(F)F)c2)cc1" ] }, "k": { "reactants": [ "C=C(C)C(=O)Nc1nccs1" ], "products": [ "Cc1ccc(S(=O)(=O)C[C@](C)(O)C(=O)Nc2nccs2)cc1" ] }, "l": { "reactants": [ "C=CC(=O)Nc1ccccc1" ], "products": [ "Cc1ccc(S(=O)(=O)C[C@@H](O)C(=O)Nc2ccccc2)cc1" ] }, "m": { "reactants": [ "C=C(C)C(=O)NCCC" ], "products": [ "CCCNC(=O)[C@](C)(O)CS(=O)(=O)c1ccc(C)cc1" ] }, "n": { "reactants": [ "C=C(C)C(=O)NCCc1ccccc1" ], "products": [ "Cc1ccc(S(=O)(=O)C[C@](C)(O)C(=O)NCCc2ccccc2)cc1" ] } } }, { "file_name": "ejoc.202300506 example 1.png", "reaction_template": { "reactants": [ "*SC1CC2=C(OC1(C)C)c1ccccc1C(=O)C2=O" ], "products": [ "*S(=O)(=O)C1CC2=C(OC1(C)C)c1ccccc1C(=O)C2=O" ] }, "detailed_reactions": { "a": { "reactants": [ "CC1(C)OC2=C(CC1Sc1ccccc1)C(=O)C(=O)c1ccccc12" ], "products": [ "CC1(C)OC2=C(CC1S(=O)(=O)c1ccccc1)C(=O)C(=O)c1ccccc12" ] }, "b": { "reactants": [ "Cc1ccc(SC2CC3=C(OC2(C)C)c2ccccc2C(=O)C3=O)cc1" ], "products": [ "Cc1ccc(S(=O)(=O)C2CC3=C(OC2(C)C)c2ccccc2C(=O)C3=O)cc1" ] }, "c": { "reactants": [ "COc1ccc(SC2CC3=C(OC2(C)C)c2ccccc2C(=O)C3=O)cc1" ], "products": [ "COc1ccc(S(=O)(=O)C2CC3=C(OC2(C)C)c2ccccc2C(=O)C3=O)cc1" ] }, "d": { "reactants": [ "CC1(C)OC2=C(CC1Sc1ccc(Cl)cc1)C(=O)C(=O)c1ccccc12" ], "products": [ "CC1(C)OC2=C(CC1S(=O)(=O)c1ccc(Cl)cc1)C(=O)C(=O)c1ccccc12" ] }, "e": { "reactants": [ "CC1(C)OC2=C(CC1Sc1ccc(F)cc1)C(=O)C(=O)c1ccccc12" ], "products": [ "CC1(C)OC2=C(CC1S(=O)(=O)c1ccc(F)cc1)C(=O)C(=O)c1ccccc12" ] }, "f": { "reactants": [ "CSC1CC2=C(OC1(C)C)c1ccccc1C(=O)C2=O" ], "products": [ "CC1(C)OC2=C(CC1S(C)(=O)=O)C(=O)C(=O)c1ccccc12" ] } } }, { "file_name": "ajoc.202300258 example 1.png", "reaction_template": { "reactants": [ "*/C=N/Nc1ccccc1", "O=C1C=CCCCC1" ], "products": [ "*c1nn(-c2ccccc2)c2c1C(=O)CCCC2" ] }, "detailed_reactions": { "bc": { "reactants": [ "COc1ccc(C=NNc2ccccc2)cc1", "O=C1C=CCCCC1" ], "products": [ "COc1ccc(-c2nn(-c3ccccc3)c3c2C(=O)CCCC3)cc1" ] }, "ac": { "reactants": [ "C(=NNc1ccccc1)c1ccccc1", "O=C1C=CCCCC1" ], "products": [ "O=C1CCCCc2c1c(-c1ccccc1)nn2-c1ccccc1" ] }, "dc": { "reactants": [ "Cc1ccc(C=NNc2ccccc2)cc1", "O=C1C=CCCCC1" ], "products": [ "Cc1ccc(-c2nn(-c3ccccc3)c3c2C(=O)CCCC3)cc1" ] }, "gc": { "reactants": [ "Brc1ccc(C=NNc2ccccc2)cc1", "O=C1C=CCCCC1" ], "products": [ "O=C1CCCCc2c1c(-c1ccc(Br)cc1)nn2-c1ccccc1" ] } } }, { "file_name": "ajoc.202300258 example 2.png", "reaction_template": { "reactants": [ "*/C=N/Nc1ccccc1", "O=C1C=CCC1" ], "products": [ "*c1nn(-c2ccccc2)c2c1C(=O)CC2" ] }, "detailed_reactions": { "ab": { "reactants": [ "C(=NNc1ccccc1)c1ccccc1", "O=C1C=CCC1" ], "products": [ "O=C1CCc2c1c(-c1ccccc1)nn2-c1ccccc1" ] }, "bb": { "reactants": [ "COc1ccc(C=NNc2ccccc2)cc1", "O=C1C=CCC1" ], "products": [ "COc1ccc(-c2nn(-c3ccccc3)c3c2C(=O)CC3)cc1" ] }, "cb": { "reactants": [ "Oc1ccccc1C=NNc1ccccc1", "O=C1C=CCC1" ], "products": [ "O=C1CCc2c1c(-c1ccccc1O)nn2-c1ccccc1" ] }, "db": { "reactants": [ "Cc1ccc(C=NNc2ccccc2)cc1", "O=C1C=CCC1" ], "products": [ "Cc1ccc(-c2nn(-c3ccccc3)c3c2C(=O)CC3)cc1" ] }, "gb": { "reactants": [ "Brc1ccc(C=NNc2ccccc2)cc1", "O=C1C=CCC1" ], "products": [ "O=C1CCc2c1c(-c1ccc(Br)cc1)nn2-c1ccccc1" ] }, "kb": { "reactants": [ "C(=NNc1ccccc1)c1ccsc1", "O=C1C=CCC1" ], "products": [ "O=C1CCc2c1c(-c1ccsc1)nn2-c1ccccc1" ] } } }, { "file_name": "ajoc.202300261 example 1.png", "reaction_template": { "reactants": [ "*NCc1ccccc1" ], "products": [ "*/N=C/c1ccccc1" ] }, "detailed_reactions": { "a": { "reactants": [ "c1ccc(CCNCc2ccccc2)cc1" ], "products": [ "C(=N/CCc1ccccc1)\\c1ccccc1" ] }, "b": { "reactants": [ "CCCCCCCNCc1ccccc1" ], "products": [ "CCCCCCC/N=C/c1ccccc1" ] }, "c": { "reactants": [ "C=CCCCNCc1ccccc1" ], "products": [ "C=CCCC/N=C/c1ccccc1" ] }, "d": { "reactants": [ "c1ccc(CNCc2ccccc2)cc1" ], "products": [ "C(=N/Cc1ccccc1)\\c1ccccc1" ] }, "e": { "reactants": [ "c1ccc(CNc2ccccc2)cc1" ], "products": [ "C(=N/c1ccccc1)\\c1ccccc1" ] }, "f": { "reactants": [ "COc1ccc(NCc2ccccc2)cc1" ], "products": [ "COc1ccc(/N=C/c2ccccc2)cc1" ] }, "g": { "reactants": [ "c1ccc(CNc2ccc3ccccc3c2)cc1" ], "products": [ "C(=N/c1ccc2ccccc2c1)\\c1ccccc1" ] }, "h": { "reactants": [ "C#Cc1ccc(NCc2ccccc2)cc1" ], "products": [ "C#Cc1ccc(/N=C/c2ccccc2)cc1" ] } } }, { "file_name": "ajoc.202300333 example 1.png", "reaction_template": { "reactants": [ "*C(=O)OC1CC1" ], "products": [ "*C(=O)N([H])C(C)c1ccccc1" ] }, "detailed_reactions": { "a": { "reactants": [ "Cc1ccc(C(=O)OC2CC2)cc1" ], "products": [ "Cc1ccc(C(=O)NC(C)c2ccccc2)cc1" ] }, "b": { "reactants": [ "O=C(OC1CC1)c1ccc(-c2ccccc2)cc1" ], "products": [ "CC(NC(=O)c1ccc(-c2ccccc2)cc1)c1ccccc1" ] }, "c": { "reactants": [ "COc1ccc(C(=O)OC2CC2)cc1" ], "products": [ "COc1ccc(C(=O)NC(C)c2ccccc2)cc1" ] }, "d": { "reactants": [ "Cc1ccccc1C(=O)OC1CC1" ], "products": [ "Cc1ccccc1C(=O)NC(C)c1ccccc1" ] }, "e": { "reactants": [ "Cc1cccc(C(=O)OC2CC2)c1" ], "products": [ "Cc1cccc(C(=O)NC(C)c2ccccc2)c1" ] }, "f": { "reactants": [ "O=C(OC1CC1)c1ccc(Cl)cc1" ], "products": [ "CC(NC(=O)c1ccc(Cl)cc1)c1ccccc1" ] }, "g": { "reactants": [ "O=C(OC1CC1)c1ccccc1Cl" ], "products": [ "CC(NC(=O)c1ccccc1Cl)c1ccccc1" ] }, "h": { "reactants": [ "O=C(OC1CC1)c1cccc(Cl)c1" ], "products": [ "CC(NC(=O)c1cccc(Cl)c1)c1ccccc1" ] }, "i": { "reactants": [ "O=C(OC1CC1)c1ccc(C(F)(F)F)cc1" ], "products": [ "CC(NC(=O)c1ccc(C(F)(F)F)cc1)c1ccccc1" ] }, "j": { "reactants": [ "O=C(OC1CC1)c1ccccc1" ], "products": [ "CC(NC(=O)c1ccccc1)c1ccccc1" ] }, "k": { "reactants": [ "O=C(OC1CC1)c1cccc2ccccc12" ], "products": [ "CC(NC(=O)c1cccc2ccccc12)c1ccccc1" ] }, "l": { "reactants": [ "O=C(C=Cc1ccccc1)OC1CC1" ], "products": [ "CC(NC(=O)/C=C/c1ccccc1)c1ccccc1" ] }, "m": { "reactants": [ "O=C(CCc1ccccc1)OC1CC1" ], "products": [ "CC(NC(=O)CCc1ccccc1)c1ccccc1" ] }, "n": { "reactants": [ "O=C(OC1CC1)C12CC3CC(CC(C3)C1)C2" ], "products": [ "CC(NC(=O)C12CC3CC(CC(C3)C1)C2)c1ccccc1" ] }, "o": { "reactants": [ "CC(C)(C(=O)OC1CC1)c1ccccc1" ], "products": [ "CC(NC(=O)C(C)(C)c1ccccc1)c1ccccc1" ] } } }, { "file_name": "ajoc.202300436 example 1.png", "reaction_template": { "reactants": [ "*/C=C/C=C", "O=C(OC(=O)c1ccccc1)c1ccccc1" ], "products": [ "*C(C=CC)[C@H](O)c1ccccc1" ] }, "detailed_reactions": { "b": { "reactants": [ "C=CC=Cc1ccc(Cl)cc1", "O=C(OC(=O)c1ccccc1)c1ccccc1" ], "products": [ "CC=CC(c1ccc(Cl)cc1)[C@H](O)c1ccccc1" ] }, "c": { "reactants": [ "C=CC=Cc1ccc(Br)cc1", "O=C(OC(=O)c1ccccc1)c1ccccc1" ], "products": [ "CC=CC(c1ccc(Br)cc1)[C@H](O)c1ccccc1" ] }, "d": { "reactants": [ "C=CC=Cc1cccc(F)c1", "O=C(OC(=O)c1ccccc1)c1ccccc1" ], "products": [ "CC=CC(c1cccc(F)c1)[C@H](O)c1ccccc1" ] }, "e": { "reactants": [ "C=CC=Cc1cccc(OC)c1", "O=C(OC(=O)c1ccccc1)c1ccccc1" ], "products": [ "CC=CC(c1cccc(OC)c1)[C@@H](O)c1ccccc1" ] }, "f": { "reactants": [ "C=CC=Cc1ccc(F)cc1", "O=C(OC(=O)c1ccccc1)c1ccccc1" ], "products": [ "CC=CC(c1ccc(F)cc1)[C@H](O)c1ccccc1" ] }, "g": { "reactants": [ "C=CC=Cc1ccc(OC)cc1", "O=C(OC(=O)c1ccccc1)c1ccccc1" ], "products": [ "CC=CC(c1ccc(OC)cc1)[C@@H](O)c1ccccc1" ] }, "h": { "reactants": [ "C=CC=Cc1ccccc1C", "O=C(OC(=O)c1ccccc1)c1ccccc1" ], "products": [ "CC=CC(c1ccccc1C)[C@@H](O)c1ccccc1" ] }, "i": { "reactants": [ "C=CC=Cc1ccccc1Br", "O=C(OC(=O)c1ccccc1)c1ccccc1" ], "products": [ "CC=CC(c1ccccc1Br)[C@H](O)c1ccccc1" ] }, "j": { "reactants": [ "C=CC=Cc1ccccc1Cl", "O=C(OC(=O)c1ccccc1)c1ccccc1" ], "products": [ "CC=CC(c1ccccc1Cl)[C@H](O)c1ccccc1" ] }, "k": { "reactants": [ "C=CC=Cc1ccc2ccccc2c1", "O=C(OC(=O)c1ccccc1)c1ccccc1" ], "products": [ "CC=CC(c1ccc2ccccc2c1)[C@H](O)c1ccccc1" ] }, "l": { "reactants": [ "C=CC=Cc1ccco1", "O=C(OC(=O)c1ccccc1)c1ccccc1" ], "products": [ "CC=CC(c1ccco1)[C@H](O)c1ccccc1" ] }, "m": { "reactants": [ "C=CC=Cc1ccoc1", "O=C(OC(=O)c1ccccc1)c1ccccc1" ], "products": [ "CC=CC(c1ccoc1)[C@H](O)c1ccccc1" ] }, "n": { "reactants": [ "C=CC=Cc1cccs1", "O=C(OC(=O)c1ccccc1)c1ccccc1" ], "products": [ "CC=CC(c1cccs1)[C@H](O)c1ccccc1" ] }, "o": { "reactants": [ "C=CC=Cc1ccsc1", "O=C(OC(=O)c1ccccc1)c1ccccc1" ], "products": [ "CC=CC(c1ccsc1)[C@H](O)c1ccccc1" ] } } }, { "file_name": "ajoc.202300436 example 2.png", "reaction_template": { "reactants": [ "C=CC=Cc1ccccc1", "*C(=O)OC(*)=O" ], "products": [ "*[C@H](O)C(C=CC)c1ccccc1" ] }, "detailed_reactions": { "a": { "reactants": [ "C=CC=Cc1ccccc1", "O=C(OC(=O)c1ccc(Cl)cc1)c1ccc(Cl)cc1" ], "products": [ "CC=CC(c1ccccc1)[C@@H](O)c1ccc(Cl)cc1" ] }, "b": { "reactants": [ "C=CC=Cc1ccccc1", "O=C(OC(=O)c1cc(OC)ccc1)c1cc(OC)ccc1" ], "products": [ "CC=CC(c1ccccc1)[C@@H](O)c1cc(OC)ccc1" ] }, "c": { "reactants": [ "C=CC=Cc1ccccc1", "O=C(OC(=O)c1ccc(F)cc1)c1ccc(F)cc1" ], "products": [ "CC=CC(c1ccccc1)[C@H](O)c1ccc(F)cc1" ] }, "d": { "reactants": [ "C=CC=Cc1ccccc1", "Cc1ccccc1C(=O)OC(=O)c1ccccc1C" ], "products": [ "CC=CC(c1ccccc1)[C@@H](O)c1ccccc1C" ] }, "e": { "reactants": [ "C=CC=Cc1ccccc1", "O=C(OC(=O)c1ccc2ccccc2c1)c1ccc2ccccc2c1" ], "products": [ "CC=CC(c1ccccc1)[C@H](O)c1ccc2ccccc2c1" ] }, "f": { "reactants": [ "C=CC=Cc1ccccc1", "O=C(OC(=O)c1ccco1)c1ccco1" ], "products": [ "CC=CC(c1ccccc1)[C@H](O)c1ccco1" ] }, "g": { "reactants": [ "C=CC=Cc1ccccc1", "O=C(OC(=O)c1ccoc1)c1ccoc1" ], "products": [ "CC=CC(c1ccccc1)[C@H](O)c1ccoc1" ] }, "h": { "reactants": [ "C=CC=Cc1ccccc1", "O=C(OC(=O)c1cccs1)c1cccs1" ], "products": [ "CC=CC(c1ccccc1)[C@H](O)c1cccs1" ] }, "i ": { "reactants": [ "C=CC=Cc1ccccc1", "O=C(OC(=O)c1ccsc1)c1ccsc1" ], "products": [ "CC=CC(c1ccccc1)[C@H](O)c1ccsc1" ] }, "j": { "reactants": [ "C=CC=Cc1ccccc1", "O=C(CCc1ccccc1)OC(=O)CCc1ccccc1" ], "products": [ "CC=CC(c1ccccc1)[C@@H](O)CCc1ccccc1" ] }, "k": { "reactants": [ "C=CC=Cc1ccccc1", "O=C(OC(=O)C1CCCCC1)C1CCCCC1" ], "products": [ "CC=CC(c1ccccc1)[C@@H](O)C1CCCCC1" ] }, "l": { "reactants": [ "C=CC=Cc1ccccc1", "CC(C)(C)C(=O)OC(=O)C(C)(C)C" ], "products": [ "CC=CC(c1ccccc1)[C@@H](O)C(C)(C)C" ] }, "m": { "reactants": [ "C=CC=Cc1ccccc1", "O=C(OC(=O)C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2" ], "products": [ "CC=CC(c1ccccc1)[C@@H](O)C12CC3CC(CC(C3)C1)C2" ] }, "n": { "reactants": [ "C=CC=Cc1ccccc1", "CC(C)(Oc1ccc(Cl)cc1)C(=O)OC(=O)C(C)(C)Oc1ccc(Cl)cc1" ], "products": [ "CC=CC(c1ccccc1)[C@@H](O)C(C)(C)Oc1ccc(Cl)cc1" ] } } }, { "file_name": "ajoc.202300468 example 1.png", "reaction_template": { "reactants": [ "[1*]C=C=CN(C/C=C(\\[2*])C)S(=O)(=O)c1ccc(C)cc1" ], "products": [ "[1*][C@@H]C1=CN(S(=O)(=O)c2ccc(C)cc2)C[C@@H]1C([2*])=C" ] }, "detailed_reactions": { "a": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C=C=C)CC=CC)cc1" ], "products": [ "C=C[C@@H]1CN(S(=O)(=O)c2ccc(C)cc2)C=C1[C@H]" ] }, "b": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C=C=Cc2ccccc2)CC=CC)cc1" ], "products": [ "C=C[C@@H]1CN(S(=O)(=O)c2ccc(C)cc2)C=C1[C@H]c1ccccc1" ] }, "c": { "reactants": [ "COc1ccc(C=C=CN(CC=CC)S(=O)(=O)c2ccc(C)cc2)cc1" ], "products": [ "C=C[C@H]1CN(S(=O)(=O)c2ccc(C)cc2)C=C1[C@H]c1ccc(OC)cc1" ] }, "d": { "reactants": [ "Cc1ccc(C=C=CN(CC=CC)S(=O)(=O)c2ccc(C)cc2)cc1" ], "products": [ "C=C[C@H]1CN(S(=O)(=O)c2ccc(C)cc2)C=C1[C@H]c1ccc(C)cc1" ] }, "e": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C=C=Cc2cccc(C)c2)CC=CC)cc1" ], "products": [ "C=C[C@H]1CN(S(=O)(=O)c2ccc(C)cc2)C=C1[C@H]c1cccc(C)c1" ] }, "f": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C=C=Cc2ccc(F)cc2)CC=CC)cc1" ], "products": [ "C=C[C@H]1CN(S(=O)(=O)c2ccc(C)cc2)C=C1[C@H]c1ccc(F)cc1" ] }, "g": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C=C=Cc2cccc(F)c2)CC=CC)cc1" ], "products": [ "C=C[C@H]1CN(S(=O)(=O)c2ccc(C)cc2)C=C1[C@H]c1cccc(F)c1" ] }, "h": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C=C=Cc2ccc(Cl)cc2)CC=CC)cc1" ], "products": [ "C=C[C@H]1CN(S(=O)(=O)c2ccc(C)cc2)C=C1[C@H]c1ccc(Cl)cc1" ] }, "i": { "reactants": [ "Cc1ccc(S(=O)(=O)N(C=C=Cc2cccc(Cl)c2)CC=CC)cc1" ], "products": [ "C=C[C@H]1CN(S(=O)(=O)c2ccc(C)cc2)C=C1[C@H]c1cccc(Cl)c1" ] }, "j": { "reactants": [ "C=C=CN(C/C=C(\\C)C)S(=O)(=O)c1ccc(C)cc1" ], "products": [ "CC1=CN(S(=O)(=O)c2ccc(C)cc2)C[C@@H]1C(=C)C" ] }, "k": { "reactants": [ "c1ccccc1C=C=CN(C/C=C(\\C)C)S(=O)(=O)c1ccc(C)cc1" ], "products": [ "C(-c1ccccc1)C1=CN(S(=O)(=O)c2ccc(C)cc2)C[C@@H]1C(=C)C" ] }, "l": { "reactants": [ "c1cc(OC)ccc1C=C=CN(C/C=C(\\C)C)S(=O)(=O)c1ccc(C)cc1" ], "products": [ "C(-c1ccc(OC)cc1)C1=CN(S(=O)(=O)c2ccc(C)cc2)C[C@@H]1C(=C)C" ] }, "m": { "reactants": [ "C1CC=CCC1N(S(=O)(=O)c2ccc(C)cc2)C=C=C" ], "products": [ "Cc1ccc(S(=O)(=O)N2C=C(C)[C@H]3C=CCCC32)cc1" ] }, "n": { "reactants": [ "C1CC=CCC1N(S(=O)(=O)c2ccc(C)cc2)C=C=Cc1ccccc1" ], "products": [ "Cc1ccc(S(=O)(=O)N2C=C(Cc3ccccc3)[C@H]3C=CCCC32)cc1" ] }, "o": { "reactants": [ "CS(=O)(=O)N(C=C=C)CC=CC" ], "products": [ "C=C[C@@H]1CN(S(=O)(=O)C)C=C1[C@H]" ] } } }, { "file_name": "ajoc.202200622 example 1.png", "reaction_template": { "reactants": [ "CC=C=CC(=O)OCc1ccccc1", "*C(=O)C=Cc1ccccc1" ], "products": [ "*C(=O)[C@@H]1[C@@H](C)C=C(C(=O)OCc2ccccc2)[C@H]1c1ccccc1" ] }, "detailed_reactions": { "a": { "reactants": [ "CC=C=CC(=O)OCc1ccccc1", "O=C(C=Cc1ccccc1)c1ccccc1" ], "products": [ "C[C@H]1C=C(C(=O)OCc2ccccc2)[C@@H](c2ccccc2)[C@@H]1C(=O)c1ccccc1" ] }, "b": { "reactants": [ "CC=C=CC(=O)OCc1ccccc1", "O=C(C=Cc1ccccc1)c1ccc(Cl)cc1" ], "products": [ "C[C@H]1C=C(C(=O)OCc2ccccc2)[C@@H](c2ccccc2)[C@@H]1C(=O)c1ccc(Cl)cc1" ] }, "c": { "reactants": [ "CC=C=CC(=O)OCc1ccccc1", "COc1ccc(C(=O)C=Cc2ccccc2)cc1" ], "products": [ "COc1ccc(C(=O)[C@@H]2[C@@H](C)C=C(C(=O)OCc3ccccc3)[C@H]2c2ccccc2)cc1" ] }, "d": { "reactants": [ "CC=C=CC(=O)OCc1ccccc1", "O=C(C=Cc1ccccc1)c1ccccc1" ], "products": [ "C[C@H]1C=C(C(=O)OCc2ccccc2)[C@@H](c2ccccc2)[C@@H]1C(=O)c1ccccc1" ] } } }, { "file_name": "ajoc.202200622 example 2.png", "reaction_template": { "reactants": [ "[H]C(C)=C=C([H])C(=O)OCC", "*C=C(C#N)C#N" ], "products": [ "*[C@@H]1C(C(=O)OCC)=C[C@@H](C)C1(C#N)C#N" ] }, "detailed_reactions": { "a": { "reactants": [ "CC=C=CC(=O)OCC", "N#CC(C#N)=Cc1ccccc1" ], "products": [ "CCOC(=O)C1=C[C@@H](C)C(C#N)(C#N)[C@@H]1c1ccccc1" ] }, "b": { "reactants": [ "CC=C=CC(=O)OCC", "N#CC(C#N)=Cc1ccc(Br)cc1" ], "products": [ "CCOC(=O)C1=C[C@@H](C)C(C#N)(C#N)[C@@H]1c1ccc(Br)cc1" ] }, "c": { "reactants": [ "CC=C=CC(=O)OCC", "N#CC(C#N)=Cc1cccc(F)c1" ], "products": [ "CCOC(=O)C1=C[C@@H](C)C(C#N)(C#N)[C@@H]1c1cccc(F)c1" ] }, "d": { "reactants": [ "CC=C=CC(=O)OCC", "N#CC(C#N)=Cc1ccc2ccccc2c1" ], "products": [ "CCOC(=O)C1=C[C@@H](C)C(C#N)(C#N)[C@@H]1c1ccc2ccccc2c1" ] } } }, { "file_name": "ajoc.202200622 example 3.png", "reaction_template": { "reactants": [ "CC=C=CC(=O)OCC", "*C(=O)C1=CCC(C)(C)C1" ], "products": [ "*C(=O)[C@@]12C(=O)C(C)(C)CC1C(C(=O)OCC)=C[C@@H]2C" ] }, "detailed_reactions": { "a": { "reactants": [ "CC=C=CC(=O)OCC", "CC1(C)CC=C(C(=O)c2ccccc2)C1" ], "products": [ "CCOC(=O)C1=C[C@H](C)[C@]2(C(=O)c3ccccc3)C(=O)C(C)(C)CC12" ] }, "b": { "reactants": [ "CC=C=CC(=O)OCC", "CC(C)C(=O)C1=CCC(C)(C)C1" ], "products": [ "CCOC(=O)C1=C[C@H](C)[C@]2(C(=O)C(C)C)C(=O)C(C)(C)CC12" ] }, "c": { "reactants": [ "CC=C=CC(=O)OCC", "CC1(C)CC=C(C(=O)c2cccc(-c3ccc(Cl)cc3)c2)C1" ], "products": [ "CCOC(=O)C1=C[C@H](C)[C@]2(C(=O)c3cccc(-c4ccc(Cl)cc4)c3)C(=O)C(C)(C)CC12" ] }, "d": { "reactants": [ "CC=C=CC(=O)OCC", "CC1(C)CC=C(C(=O)C(C)(C)C)C1" ], "products": [ "CCOC(=O)C1=C[C@H](C)[C@]2(C(=O)C(C)(C)C)C(=O)C(C)(C)CC12" ] } } }, { "file_name": "ajoc.202200383 example 1.png", "reaction_template": { "reactants": [ "*/C=C/C([H])=O", "[1*]c1ccccc1NC1=CC(=O)N([2*])C1=O" ], "products": [ "*c1cc(=O)n(-c2ccccc2[7*])c2c1C(=O)N([2*])C2=O" ] }, "detailed_reactions": { "a": { "reactants": [ "c1ccccc1C=CC=O", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "c1ccccc1-c1cc(=O)n(-c2ccccc2C(C)(C)C)c2c1C(=O)N(Cc1ccccc1)C2=O" ] }, "b": { "reactants": [ "c1cc(C)ccc1C=CC=O", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "c1cc(C)ccc1-c1cc(=O)n(-c2ccccc2C(C)(C)C)c2c1C(=O)N(Cc1ccccc1)C2=O" ] }, "c": { "reactants": [ "c1cc(CC)ccc1C=CC=O", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "c1cc(CC)ccc1-c1cc(=O)n(-c2ccccc2C(C)(C)C)c2c1C(=O)N(Cc1ccccc1)C2=O" ] }, "d": { "reactants": [ "c1cc(C(C)C)ccc1C=CC=O", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "c1cc(C(C)C)ccc1-c1cc(=O)n(-c2ccccc2C(C)(C)C)c2c1C(=O)N(Cc1ccccc1)C2=O" ] }, "e": { "reactants": [ "c1cc(OC)ccc1C=CC=O", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "c1cc(OC)ccc1-c1cc(=O)n(-c2ccccc2C(C)(C)C)c2c1C(=O)N(Cc1ccccc1)C2=O" ] }, "f": { "reactants": [ "c1cc(C(C)(C)C)ccc1C=CC=O", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "c1cc(C(C)(C)C)ccc1-c1cc(=O)n(-c2ccccc2C(C)(C)C)c2c1C(=O)N(Cc1ccccc1)C2=O" ] }, "g": { "reactants": [ "c1cc(N(C)C)ccc1C=CC=O", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "c1cc(N(C)C)ccc1-c1cc(=O)n(-c2ccccc2C(C)(C)C)c2c1C(=O)N(Cc1ccccc1)C2=O" ] }, "h": { "reactants": [ "c1cc(Cl)ccc1C=CC=O", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "c1cc(Cl)ccc1-c1cc(=O)n(-c2ccccc2C(C)(C)C)c2c1C(=O)N(Cc1ccccc1)C2=O" ] }, "i": { "reactants": [ "c1cc(Br)ccc1C=CC=O", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "c1cc(Br)ccc1-c1cc(=O)n(-c2ccccc2C(C)(C)C)c2c1C(=O)N(Cc1ccccc1)C2=O" ] }, "j": { "reactants": [ "c1cc(C#N)ccc1C=CC=O", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "c1cc(C#N)ccc1-c1cc(=O)n(-c2ccccc2C(C)(C)C)c2c1C(=O)N(Cc1ccccc1)C2=O" ] }, "k": { "reactants": [ "c1cc([N+](=O)[O-])ccc1C=CC=O", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "c1cc([N+](=O)[O-])ccc1-c1cc(=O)n(-c2ccccc2C(C)(C)C)c2c1C(=O)N(Cc1ccccc1)C2=O" ] }, "l": { "reactants": [ "COc1ccccc1C=CC=O", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "COc1ccccc1-c1cc(=O)n(-c2ccccc2C(C)(C)C)c2c1C(=O)N(Cc1ccccc1)C2=O" ] }, "m": { "reactants": [ "Cc1ccccc1C=CC=O", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "Cc1ccccc1-c1cc(=O)n(-c2ccccc2C(C)(C)C)c2c1C(=O)N(Cc1ccccc1)C2=O" ] }, "n": { "reactants": [ "Brc1ccccc1C=CC=O", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "Brc1ccccc1-c1cc(=O)n(-c2ccccc2C(C)(C)C)c2c1C(=O)N(Cc1ccccc1)C2=O" ] }, "o": { "reactants": [ "O=CC=Cc1cccc(OC)c1", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "CC(C)(C)c1ccccc1-n1c2c(c(-c3cccc(OC)c3)cc1=O)C(=O)N(Cc1ccccc1)C2=O" ] }, "p": { "reactants": [ "O=CC=Cc1cccc(Cl)c1", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "CC(C)(C)c1ccccc1-n1c2c(c(-c3cccc(Cl)c3)cc1=O)C(=O)N(Cc1ccccc1)C2=O" ] }, "q": { "reactants": [ "Cc1cccc(C=CC=O)c1", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "Cc1cccc(-c2cc(=O)n(-c3ccccc3C(C)(C)C)c3c2C(=O)N(Cc2ccccc2)C3=O)c1" ] }, "r": { "reactants": [ "Cc1ccc(C=CC=O)cc1C", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "Cc1ccc(-c2cc(=O)n(-c3ccccc3C(C)(C)C)c3c2C(=O)N(Cc2ccccc2)C3=O)cc1C" ] }, "s": { "reactants": [ "O=CC=Cc1cnccc1", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "CC(C)(C)c1ccccc1-n1c2c(c(-c3cnccc3)cc1=O)C(=O)N(Cc1ccccc1)C2=O" ] }, "t": { "reactants": [ "O=CC=Cc1ccco1", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "CC(C)(C)c1ccccc1-n1c2c(c(-c3ccco3)cc1=O)C(=O)N(Cc1ccccc1)C2=O" ] }, "u": { "reactants": [ "O=CC=Cc1cccs1", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "CC(C)(C)c1ccccc1-n1c2c(c(-c3cccs3)cc1=O)C(=O)N(Cc1ccccc1)C2=O" ] }, "v": { "reactants": [ "O=CC=Cc1cscc1", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "CC(C)(C)c1ccccc1-n1c2c(c(-c3cscc3)cc1=O)C(=O)N(Cc1ccccc1)C2=O" ] }, "w": { "reactants": [ "O=CC=Cc1ccc2ccccc2c1", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "CC(C)(C)c1ccccc1-n1c2c(c(-c3cc4ccccc4cc3)cc1=O)C(=O)N(Cc1ccccc1)C2=O" ] }, "x": { "reactants": [ "O=CC=CC#Cc1ccccc1", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "CC(C)(C)c1ccccc1-n1c2c(c(C#Cc3ccccc3)cc1=O)C(=O)N(Cc1ccccc1)C2=O" ] }, "y": { "reactants": [ "O=CC=CC=Cc1ccco1", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "CC(C)(C)c1ccccc1-n1c2c(c(/C=C/c3ccco3)cc1=O)C(=O)N(Cc1ccccc1)C2=O" ] }, "z": { "reactants": [ "O=CC=CC", "CC(C)(C)c1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "CC(C)(C)c1ccccc1-n1c2c(c(C)cc1=O)C(=O)N(Cc1ccccc1)C2=O" ] }, "aa": { "reactants": [ "O=CC=Cc1ccccc1", "CC(C)(C)c1cc(Br)ccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "Brc1ccc(-n2c3c(c(-c4ccccc4)cc2=O)C(=O)N(Cc2ccccc2)C3=O)c(C(C)(C)C)c1" ] }, "ab": { "reactants": [ "O=CC=Cc1ccccc1", "CC(C)(C)c1cc(I)ccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "Ic1ccc(-n2c3c(c(-c4ccccc4)cc2=O)C(=O)N(Cc2ccccc2)C3=O)c(C(C)(C)C)c1" ] }, "ac": { "reactants": [ "O=CC=Cc1ccccc1", "CC(C)(C)c1cc(-c2ccccc2)ccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "c1ccccc1-c1ccc(-n2c3c(c(-c4ccccc4)cc2=O)C(=O)N(Cc2ccccc2)C3=O)c(C(C)(C)C)c1" ] }, "ad": { "reactants": [ "O=CC=Cc1ccccc1", "Ic1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "Ic1ccccc1-n1c2c(c(-c3ccccc3)cc1=O)C(=O)N(Cc1ccccc1)C2=O" ] }, "ae": { "reactants": [ "O=CC=Cc1ccccc1", "Brc1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "Brc1ccccc1-n1c2c(c(-c3ccccc3)cc1=O)C(=O)N(Cc1ccccc1)C2=O" ] }, "af": { "reactants": [ "O=CC=Cc1ccccc1", "C(C)Cc1ccccc1NC1=CC(=O)N(Cc2ccccc2)C1=O" ], "products": [ "C(C)Cc1ccccc1-n1c2c(c(-c3ccccc3)cc1=O)C(=O)N(Cc1ccccc1)C2=O" ] }, "ag": { "reactants": [ "O=CC=Cc1ccccc1", "CCCCN1C(=O)C=C(Nc2ccccc2C(C)(C)C)C1=O" ], "products": [ "CCCCN1C(=O)c2c(-c3ccccc3)cc(=O)n(-c3ccccc3C(C)(C)C)c2C1=O" ] } } }, { "file_name": "ajoc.202200603 example 1.png", "reaction_template": { "reactants": [ "*c1ccc2c(=O)n([H])c(-c3c(F)c(F)c(-c4ccc(OC)cc4)c4nsnc34)cc2c1" ], "products": [ "*c1ccc2c(OS(=O)(=O)C(F)(F)F)nc(-c3c(F)c(F)c(-c4ccc(OC)cc4)c4nsnc34)cc2c1" ] }, "detailed_reactions": { "a": { "reactants": [ "COc1ccc(-c2c(F)c(F)c(-c3cc4ccccc4c(=O)[nH]3)c3nsnc23)cc1" ], "products": [ "COc1ccc(-c2c(F)c(F)c(-c3cc4ccccc4c(OS(=O)(=O)C(F)(F)F)n3)c3nsnc23)cc1" ] }, "b": { "reactants": [ "COc1ccc(-c2c(F)c(F)c(-c3cc4cc(C)ccc4c(=O)[nH]3)c3nsnc23)cc1" ], "products": [ "COc1ccc(-c2c(F)c(F)c(-c3cc4cc(C)ccc4c(OS(=O)(=O)C(F)(F)F)n3)c3nsnc23)cc1" ] }, "c": { "reactants": [ "COc1ccc(-c2c(F)c(F)c(-c3cc4cc(OC)ccc4c(=O)[nH]3)c3nsnc23)cc1" ], "products": [ "COc1ccc(-c2c(F)c(F)c(-c3cc4cc(OC)ccc4c(OS(=O)(=O)C(F)(F)F)n3)c3nsnc23)cc1" ] }, "d": { "reactants": [ "COc1ccc(-c2c(F)c(F)c(-c3cc4cc(F)ccc4c(=O)[nH]3)c3nsnc23)cc1" ], "products": [ "COc1ccc(-c2c(F)c(F)c(-c3cc4cc(F)ccc4c(OS(=O)(=O)C(F)(F)F)n3)c3nsnc23)cc1" ] }, "e": { "reactants": [ "COc1ccc(-c2c(F)c(F)c(-c3cc4cc(C(F)(F)F)ccc4c(=O)[nH]3)c3nsnc23)cc1" ], "products": [ "COc1ccc(-c2c(F)c(F)c(-c3cc4cc(C(F)(F)F)ccc4c(OS(=O)(=O)C(F)(F)F)n3)c3nsnc23)cc1" ] }, "f": { "reactants": [ "COc1ccc(-c2c(F)c(F)c(-c3cc4sccc4c(=O)[nH]3)c3nsnc23)cc1" ], "products": [ "COc1ccc(-c2c(F)c(F)c(-c3cc4sccc4c(OS(=O)(=O)C(F)(F)F)n3)c3nsnc23)cc1" ] } } }, { "file_name": "ajoc.202200531 example 1.png", "reaction_template": { "reactants": [ "*C(=C)C1(O[Si](C)(C)C)CCC1", "[1*]NS(=O)(=O)c1ccccc1" ], "products": [ "*C1(CN([1*])S(=O)(=O)c2ccccc2)CCCC1=O" ] }, "detailed_reactions": { "a": { "reactants": [ "C=C(c1ccccc1)C1(O[Si](C)(C)C)CCC1", "O=S(=O)(NS(=O)(=O)c1ccccc1)c1ccccc1" ], "products": [ "O=C1CCCC1(CN(S(=O)(=O)c1ccccc1)S(=O)(=O)c1ccccc1)c1ccccc1" ] }, "b": { "reactants": [ "C=C(c1ccc(C)cc1)C1(O[Si](C)(C)C)CCC1", "O=S(=O)(NS(=O)(=O)c1ccccc1)c1ccccc1" ], "products": [ "Cc1ccc(C2(CN(S(=O)(=O)c3ccccc3)S(=O)(=O)c3ccccc3)CCCC2=O)cc1" ] }, "c": { "reactants": [ "C=C(c1ccc(C(C)(C)C)cc1)C1(O[Si](C)(C)C)CCC1", "O=S(=O)(NS(=O)(=O)c1ccccc1)c1ccccc1" ], "products": [ "CC(C)(C)c1ccc(C2(CN(S(=O)(=O)c3ccccc3)S(=O)(=O)c3ccccc3)CCCC2=O)cc1" ] }, "d": { "reactants": [ "C=C(c1ccc(OC)cc1)C1(O[Si](C)(C)C)CCC1", "O=S(=O)(NS(=O)(=O)c1ccccc1)c1ccccc1" ], "products": [ "COc1ccc(C2(CN(S(=O)(=O)c3ccccc3)S(=O)(=O)c3ccccc3)CCCC2=O)cc1" ] }, "e": { "reactants": [ "C=C(c1ccc(F)cc1)C1(O[Si](C)(C)C)CCC1", "O=S(=O)(NS(=O)(=O)c1ccccc1)c1ccccc1" ], "products": [ "O=C1CCCC1(CN(S(=O)(=O)c1ccccc1)S(=O)(=O)c1ccccc1)c1ccc(F)cc1" ] }, "f": { "reactants": [ "C=C(c1ccc(Cl)cc1)C1(O[Si](C)(C)C)CCC1", "O=S(=O)(NS(=O)(=O)c1ccccc1)c1ccccc1" ], "products": [ "O=C1CCCC1(CN(S(=O)(=O)c1ccccc1)S(=O)(=O)c1ccccc1)c1ccc(Cl)cc1" ] }, "g": { "reactants": [ "C=C(c1cccc(C)c1)C1(O[Si](C)(C)C)CCC1", "O=S(=O)(NS(=O)(=O)c1ccccc1)c1ccccc1" ], "products": [ "Cc1cccc(C2(CN(S(=O)(=O)c3ccccc3)S(=O)(=O)c3ccccc3)CCCC2=O)c1" ] }, "h": { "reactants": [ "C=C(c1cccc(F)c1)C1(O[Si](C)(C)C)CCC1", "O=S(=O)(NS(=O)(=O)c1ccccc1)c1ccccc1" ], "products": [ "O=C1CCCC1(CN(S(=O)(=O)c1ccccc1)S(=O)(=O)c1ccccc1)c1cccc(F)c1" ] }, "i": { "reactants": [ "C=C(c1ccccc1C)C1(O[Si](C)(C)C)CCC1", "O=S(=O)(NS(=O)(=O)c1ccccc1)c1ccccc1" ], "products": [ "Cc1ccccc1C1(CN(S(=O)(=O)c2ccccc2)S(=O)(=O)c2ccccc2)CCCC1=O" ] }, "j": { "reactants": [ "C=C(c1ccc(C)c(C)c1)C1(O[Si](C)(C)C)CCC1", "O=S(=O)(NS(=O)(=O)c1ccccc1)c1ccccc1" ], "products": [ "Cc1ccc(C2(CN(S(=O)(=O)c3ccccc3)S(=O)(=O)c3ccccc3)CCCC2=O)cc1C" ] }, "k": { "reactants": [ "C=C(c1ccc2ccccc2c1)C1(O[Si](C)(C)C)CCC1", "O=S(=O)(NS(=O)(=O)c1ccccc1)c1ccccc1" ], "products": [ "O=C1CCCC1(CN(S(=O)(=O)c1ccccc1)S(=O)(=O)c1ccccc1)c1ccc2ccccc2c1" ] }, "l": { "reactants": [ "C=C(c1ccccc1)C1(O[Si](C)(C)C)COC1", "O=S(=O)(NS(=O)(=O)c1ccccc1)c1ccccc1" ], "products": [ "O=C1COCC1(CN(S(=O)(=O)c1ccccc1)S(=O)(=O)c1ccccc1)c1ccccc1" ] }, "m": { "reactants": [ "C=C(c1ccccc1)C1(O[Si](C)(C)C)CCC1", "O=S(-c1ccc(Br)cc1)(=O)NS(=O)(=O)c1ccccc1" ], "products": [ "O=C1CCCC1(CN([SH](=O)=O)S(=O)(=O)c1ccc(Br)cc1)c1ccccc1" ] }, "n": { "reactants": [ "C=C(c1ccccc1)C1(O[Si](C)(C)C)CCC1", "O=S(-c1ccc([N+](=O)[O-])cc1)(=O)NS(=O)(=O)c1ccccc1" ], "products": [ "O=C1CCCC1(CN([SH](=O)=O)S(=O)(=O)c1ccc([N+](=O)[O-])cc1)c1ccccc1" ] }, "o": { "reactants": [ "C=C(c1ccccc1)C1(O[Si](C)(C)C)CCC1", "O=S(=O)(NS(=O)(=O)c1ccc2ccccc2c1)c1ccccc1" ], "products": [ "O=C1CCCC1(CN(S(=O)(=O)c1ccccc1)S(=O)(=O)c1ccc2ccccc2c1)c1ccccc1" ] } } }, { "file_name": "ajoc.202200486 example 1.png", "reaction_template": { "reactants": [ "*Cc1cc2c(cc1O)OCO2", "N#CCC#N" ], "products": [ "*C1C(C#N)=C(N)Oc2cc3c(cc21)OCO3" ] }, "detailed_reactions": { "a": { "reactants": [ "COc1ccc(Cc2cc3c(cc2O)OCO3)cc1", "N#CCC#N" ], "products": [ "COc1ccc(C2C(C#N)=C(N)Oc3cc4c(cc32)OCO4)cc1" ] }, "b": { "reactants": [ "Oc1cc2c(cc1Cc1ccccc1)OCO2", "N#CCC#N" ], "products": [ "N#CC1=C(N)Oc2cc3c(cc2C1c1ccccc1)OCO3" ] }, "c": { "reactants": [ "Cc1ccc(Cc2cc3c(cc2O)OCO3)cc1", "N#CCC#N" ], "products": [ "Cc1ccc(C2C(C#N)=C(N)Oc3cc4c(cc32)OCO4)cc1" ] }, "d": { "reactants": [ "Oc1cc2c(cc1Cc1ccc(F)cc1)OCO2", "N#CCC#N" ], "products": [ "N#CC1=C(N)Oc2cc3c(cc2C1c1ccc(F)cc1)OCO3" ] }, "e": { "reactants": [ "Oc1cc2c(cc1Cc1ccc(Cl)cc1)OCO2", "N#CCC#N" ], "products": [ "N#CC1=C(N)Oc2cc3c(cc2C1c1ccc(Cl)cc1)OCO3" ] }, "f": { "reactants": [ "Oc1cc2c(cc1Cc1ccc(Br)cc1)OCO2", "N#CCC#N" ], "products": [ "N#CC1=C(N)Oc2cc3c(cc2C1c1ccc(Br)cc1)OCO3" ] }, "g": { "reactants": [ "Cc1cccc(Cc2cc3c(cc2O)OCO3)c1", "N#CCC#N" ], "products": [ "Cc1cccc(C2C(C#N)=C(N)Oc3cc4c(cc32)OCO4)c1" ] }, "h": { "reactants": [ "Cc1ccccc1Cc1cc2c(cc1O)OCO2", "N#CCC#N" ], "products": [ "Cc1ccccc1C1C(C#N)=C(N)Oc2cc3c(cc21)OCO3" ] }, "i": { "reactants": [ "Oc1cc2c(cc1Cc1ccc3c(c1)OCO3)OCO2", "N#CCC#N" ], "products": [ "N#CC1=C(N)Oc2cc3c(cc2C1c1ccc2c(c1)OCO2)OCO3" ] } } }, { "file_name": "ajoc.202200486 example 2.png", "reaction_template": { "reactants": [ "*/C=C/Cc1cc2c(cc1O)OCO2", "N#CCC#N" ], "products": [ "*/C=C/C1C(C#N)=C(N)Oc2cc3c(cc21)OCO3" ] }, "detailed_reactions": { "a": { "reactants": [ "Oc1ccc(C=CCc2cc3c(cc2O)OCO3)cc1", "N#CCC#N" ], "products": [ "N#CC1=C(N)Oc2cc3c(cc2C1/C=C/c1ccc(O)cc1)OCO3" ] }, "b": { "reactants": [ "Oc1cc2c(cc1CC=Cc1ccccc1)OCO2", "N#CCC#N" ], "products": [ "N#CC1=C(N)Oc2cc3c(cc2C1/C=C/c1ccccc1)OCO3" ] }, "c": { "reactants": [ "Cc1ccc(C=CCc2cc3c(cc2O)OCO3)cc1", "N#CCC#N" ], "products": [ "Cc1ccc(/C=C/C2C(C#N)=C(N)Oc3cc4c(cc32)OCO4)cc1" ] }, "d": { "reactants": [ "Fc1ccc(C=CCc2cc3c(cc2O)OCO3)cc1", "N#CCC#N" ], "products": [ "N#CC1=C(N)Oc2cc3c(cc2C1/C=C/c1ccc(F)cc1)OCO3" ] }, "e": { "reactants": [ "Clc1ccc(C=CCc2cc3c(cc2O)OCO3)cc1", "N#CCC#N" ], "products": [ "N#CC1=C(N)Oc2cc3c(cc2C1/C=C/c1ccc(Cl)cc1)OCO3" ] }, "f": { "reactants": [ "Oc1cc2c(cc1CC=Cc1cccs1)OCO2", "N#CCC#N" ], "products": [ "N#CC1=C(N)Oc2cc3c(cc2C1/C=C/c1cccs1)OCO3" ] } } }, { "file_name": "ajoc.202200488 example 1.png", "reaction_template": { "reactants": [ "*OCC(=C)C" ], "products": [ "*OC=C(C)C" ] }, "detailed_reactions": { "b": { "reactants": [ "C=C(C)COc1ccc(OC)cc1" ], "products": [ "CC(C)=COc1ccc(OC)cc1" ] }, "c": { "reactants": [ "C=C(C)COc1ccc(C(=O))cc1" ], "products": [ "CC(C)=COc1ccc(C(=O))cc1" ] }, "d": { "reactants": [ "C=C(C)COc1ccc(C(=O)OC)cc1" ], "products": [ "CC(C)=COc1ccc(C(=O)OC)cc1" ] }, "e": { "reactants": [ "C=C(C)COc1ccc(CC(=O)OCC)cc1" ], "products": [ "CC(C)=COc1ccc(CC(=O)OCC)cc1" ] }, "f": { "reactants": [ "C=C(C)COc1ccc(Cl)cc1" ], "products": [ "CC(C)=COc1ccc(Cl)cc1" ] }, "g": { "reactants": [ "C=C(C)COc1ccc(Br)cc1" ], "products": [ "CC(C)=COc1ccc(Br)cc1" ] }, "h": { "reactants": [ "C=C(C)COc1ccc(CCOC(=O)C)cc1" ], "products": [ "CC(C)=COc1ccc(CCOC(=O)C)cc1" ] }, "i": { "reactants": [ "C=C(C)COc1ccc(CCO[Si](C)(C)C)cc1" ], "products": [ "CC(C)=COc1ccc(CCO[Si](C)(C)C)cc1" ] }, "j": { "reactants": [ "C=C(C)COc1cccc2ccccc12" ], "products": [ "CC(C)=COc1cccc2ccccc12" ] }, "k": { "reactants": [ "C=C(C)COc1ccc2ccccc2c1" ], "products": [ "CC(C)=COc1ccc2ccccc2c1" ] }, "l": { "reactants": [ "C=C(C)COc1ccc(OCC(=C)C)cc1" ], "products": [ "CC(C)=COc1ccc(OC=C(C)C)cc1" ] }, "m": { "reactants": [ "C=C(C)COCCCc1ccccc1" ], "products": [ "CC(C)=COCCCc1ccccc1" ] }, "n": { "reactants": [ "C=C(C)COCC1COC(C)(C)O1" ], "products": [ "CC(C)=COCC1COC(C)(C)O1" ] }, "o": { "reactants": [ "C=C(C)COC1CCN(C(=O)OC(C)(C)C)C1" ], "products": [ "CC(C)=COC1CCN(C(=O)OC(C)(C)C)C1" ] }, "p": { "reactants": [ "C=C(C)CO[C@@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCCC(C)C)[C@@]4(C)CC[C@@H]32)C1" ], "products": [ "CC(C)=CO[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCCC(C)C)[C@@]4(C)CC[C@@H]32)C1" ] }, "q": { "reactants": [ "C=C(C)COc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12" ], "products": [ "CC(C)=COc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12" ] } } }, { "file_name": "ajoc.202200488 example 2.png", "reaction_template": { "reactants": [ "*OCC(=C)C" ], "products": [ "*OC=C(C)C" ] }, "detailed_reactions": { "r": { "reactants": [ "C=C(C)COc1ccc(OCc2ccccc2)cc1" ], "products": [ "CC(C)=COc1ccc(OCc2ccccc2)cc1" ] }, "s": { "reactants": [ "C=C(C)COCCCCOCc1ccc(Br)cc1" ], "products": [ "CC(C)=COCCCCOCc1ccc(Br)cc1" ] }, "t": { "reactants": [ "C=C(C)COc1ccc(OCC=C(C)C)cc1" ], "products": [ "CC(C)=CCOc1ccc(OC=C(C)C)cc1" ] }, "u": { "reactants": [ "C=C(C)COCCCCOCC=C(C)C" ], "products": [ "CC(C)=CCOCCCCOC=C(C)C" ] }, "v": { "reactants": [ "C=C(C)COC1CCN(C(=O)OCc2ccccc2)CC1" ], "products": [ "CC(C)=COC1CCN(C(=O)OCc2ccccc2)CC1" ] }, "w": { "reactants": [ "C=C(C)COc1ccc(C(C)(C)c2ccc(OC(=O)OCc3ccccc3)cc2)cc1" ], "products": [ "CC(C)=COc1ccc(C(C)(C)c2ccc(OC(=O)OCc3ccccc3)cc2)cc1" ] }, "x": { "reactants": [ "C=C(C)COc1ccc(C[C@H](NC(=O)OC(C)(C)C)C(=O)OC)cc1" ], "products": [ "COC(=O)[C@@H](NC(=O)OC(C)(C)C)Cc1ccc(OC=C(C)C)cc1" ] }, "y": { "reactants": [ "C=C(C)COc1ccc(C[C@H](NC(=O)OCc2ccccc2)C(=O)OC)cc1" ], "products": [ "COC(=O)[C@@H](NC(=O)OCc2ccccc2)Cc1ccc(OC=C(C)C)cc1" ] } } }, { "file_name": "ajoc.202200550 example 1.png", "reaction_template": { "reactants": [ "O=C(Nc1ccccc1)C(F)(F)F", "[2*]C(=O)C#C[3*]" ], "products": [ "[2*]C(=O)/C(C(=O)C(F)(F)F)=C(\\[3*])Nc1ccccc1" ] }, "detailed_reactions": { "a": { "reactants": [ "O=C(Nc1ccccc1)C(F)(F)F", "COc1ccc(C(=O)C#Cc2ccccc2)cc1" ], "products": [ "COc1ccc(C(=O)/C(C(=O)C(F)(F)F)=C(/Nc2ccccc2)c2ccccc2)cc1" ] }, "b": { "reactants": [ "O=C(Nc1ccccc1)C(F)(F)F", "O=C(C#Cc1ccccc1)c1ccccc1" ], "products": [ "O=C(/C(C(=O)C(F)(F)F)=C(/Nc1ccccc1)c1ccccc1)c1ccccc1" ] }, "c": { "reactants": [ "O=C(Nc1ccccc1)C(F)(F)F", "Cc1ccc(C(=O)C#Cc2ccccc2)cc1" ], "products": [ "Cc1ccc(C(=O)/C(C(=O)C(F)(F)F)=C(/Nc2ccccc2)c2ccccc2)cc1" ] }, "d": { "reactants": [ "O=C(Nc1ccccc1)C(F)(F)F", "Cc1cccc(C(=O)C#Cc2ccccc2)c1" ], "products": [ "Cc1cccc(C(=O)/C(C(=O)C(F)(F)F)=C(/Nc2ccccc2)c2ccccc2)c1" ] }, "e": { "reactants": [ "O=C(Nc1ccccc1)C(F)(F)F", "O=C(C#Cc1ccccc1)c1ccc(Cl)cc1" ], "products": [ "O=C(/C(C(=O)C(F)(F)F)=C(/Nc1ccccc1)c1ccccc1)c1ccc(Cl)cc1" ] }, "f": { "reactants": [ "O=C(Nc1ccccc1)C(F)(F)F", "O=C(C#Cc1ccccc1)c1cccc(Cl)c1" ], "products": [ "O=C(/C(C(=O)C(F)(F)F)=C(/Nc1ccccc1)c1ccccc1)c1cccc(Cl)c1" ] }, "g": { "reactants": [ "O=C(Nc1ccccc1)C(F)(F)F", "O=C(C#Cc1ccccc1)c1ccc([N+](=O)[O-])cc1" ], "products": [ "O=C(/C(C(=O)C(F)(F)F)=C(/Nc1ccccc1)c1ccccc1)c1ccc([N+](=O)[O-])cc1" ] }, "h": { "reactants": [ "O=C(Nc1ccccc1)C(F)(F)F", "N#Cc1cccc(C(=O)C#Cc2ccccc2)c1" ], "products": [ "N#Cc1cccc(C(=O)/C(C(=O)C(F)(F)F)=C(/Nc2ccccc2)c2ccccc2)c1" ] }, "i": { "reactants": [ "O=C(Nc1ccccc1)C(F)(F)F", "O=C(C#Cc1ccccc1)c1cccc2ccccc12" ], "products": [ "O=C(/C(C(=O)C(F)(F)F)=C(/Nc1ccccc1)c1ccccc1)c1cccc2ccccc12" ] }, "j": { "reactants": [ "O=C(Nc1ccccc1)C(F)(F)F", "Cn1c(C(=O)C#Cc2ccccc2)cc2ccccc21" ], "products": [ "Cn1c(C(=O)/C(C(=O)C(F)(F)F)=C(/Nc2ccccc2)c2ccccc2)cc2ccccc21" ] }, "k": { "reactants": [ "O=C(Nc1ccccc1)C(F)(F)F", "O=C(C#Cc1ccccc1)c1ccco1" ], "products": [ "O=C(/C(C(=O)C(F)(F)F)=C(/Nc1ccccc1)c1ccccc1)c1ccco1" ] }, "l": { "reactants": [ "O=C(Nc1ccccc1)C(F)(F)F", "CC(C)(C)C(=O)C#Cc1ccccc1" ], "products": [ "CC(C)(C)C(=O)/C(C(=O)C(F)(F)F)=C(/Nc1ccccc1)c1ccccc1" ] }, "m": { "reactants": [ "O=C(Nc1ccccc1)C(F)(F)F", "O=C(C#Cc1ccc(F)cc1)c1ccccc1" ], "products": [ "O=C(/C(C(=O)C(F)(F)F)=C(/Nc1ccccc1)c1ccc(F)cc1)c1ccccc1" ] }, "n": { "reactants": [ "O=C(Nc1ccccc1)C(F)(F)F", "O=C(C#Cc1ccc(Cl)cc1)c1ccccc1" ], "products": [ "O=C(/C(C(=O)C(F)(F)F)=C(/Nc1ccccc1)c1ccc(Cl)cc1)c1ccccc1" ] }, "o": { "reactants": [ "O=C(Nc1ccccc1)C(F)(F)F", "O=C(C#Cc1cccc(Cl)c1)c1ccccc1" ], "products": [ "O=C(/C(C(=O)C(F)(F)F)=C(/Nc1ccccc1)c1cccc(Cl)c1)c1ccccc1" ] }, "p": { "reactants": [ "O=C(Nc1ccccc1)C(F)(F)F", "O=C(C#Cc1ccc(I)cc1)c1ccccc1" ], "products": [ "O=C(/C(C(=O)C(F)(F)F)=C(/Nc1ccccc1)c1ccc(I)cc1)c1ccccc1" ] }, "q": { "reactants": [ "O=C(Nc1ccccc1)C(F)(F)F", "O=C(C#Cc1cccs1)c1ccccc1" ], "products": [ "O=C(/C(C(=O)C(F)(F)F)=C(/Nc1ccccc1)c1cccs1)c1ccccc1" ] }, "r": { "reactants": [ "O=C(Nc1ccccc1)C(F)(F)F", "Cc1ccc(C#CC(=O)c2ccc(C)cc2)cc1" ], "products": [ "Cc1ccc(C(=O)/C(C(=O)C(F)(F)F)=C(/Nc2ccccc2)c2ccc(C)cc2)cc1" ] } } }, { "file_name": "ajoc.202200550 example 2.png", "reaction_template": { "reactants": [ "O=C(N[Rf])C(F)(F)F", "O=C(C#Cc1ccccc1)c1ccccc1" ], "products": [ "O=C(/C(C(=O)C(F)(F)F)=C(/N[Rf])c1ccccc1)c1ccccc1" ] }, "detailed_reactions": { "s": { "reactants": [ "COc1ccc(NC(=O)C(F)(F)F)cc1", "O=C(C#Cc1ccccc1)c1ccccc1" ], "products": [ "COc1ccc(N/C(=C(/C(=O)c2ccccc2)C(=O)C(F)(F)F)c2ccccc2)cc1" ] }, "t": { "reactants": [ "Cc1ccc(NC(=O)C(F)(F)F)cc1", "O=C(C#Cc1ccccc1)c1ccccc1" ], "products": [ "Cc1ccc(N/C(=C(/C(=O)c2ccccc2)C(=O)C(F)(F)F)c2ccccc2)cc1" ] }, "u": { "reactants": [ "O=C(Nc1ccc(F)cc1)C(F)(F)F", "O=C(C#Cc1ccccc1)c1ccccc1" ], "products": [ "O=C(/C(C(=O)C(F)(F)F)=C(/Nc1ccc(F)cc1)c1ccccc1)c1ccccc1" ] }, "v": { "reactants": [ "O=C(Nc1ccc(Cl)cc1)C(F)(F)F", "O=C(C#Cc1ccccc1)c1ccccc1" ], "products": [ "O=C(/C(C(=O)C(F)(F)F)=C(/Nc1ccc(Cl)cc1)c1ccccc1)c1ccccc1" ] }, "w": { "reactants": [ "O=C(Nc1ccccc1Cl)C(F)(F)F", "O=C(C#Cc1ccccc1)c1ccccc1" ], "products": [ "O=C(/C(C(=O)C(F)(F)F)=C(/Nc1ccccc1Cl)c1ccccc1)c1ccccc1" ] }, "x": { "reactants": [ "O=C(Nc1cccc(Br)c1)C(F)(F)F", "O=C(C#Cc1ccccc1)c1ccccc1" ], "products": [ "O=C(/C(C(=O)C(F)(F)F)=C(/Nc1cccc(Br)c1)c1ccccc1)c1ccccc1" ] }, "y": { "reactants": [ "CCCCNC(=O)C(F)(F)F", "O=C(C#Cc1ccccc1)c1ccccc1" ], "products": [ "CCCCN/C(=C(/C(=O)c1ccccc1)C(=O)C(F)(F)F)c1ccccc1" ] }, "z": { "reactants": [ "CC(C)CNC(=O)C(F)(F)F", "O=C(C#Cc1ccccc1)c1ccccc1" ], "products": [ "CC(C)CN/C(=C(/C(=O)c1ccccc1)C(=O)C(F)(F)F)c1ccccc1" ] } } }, { "file_name": "ajoc.202200524 example 1.png", "reaction_template": { "reactants": [ "[2*]C=C1C=C(C(C)(C)C)C(=O)C(C(C)(C)C)=C1", "[3*]S" ], "products": [ "[2*]C(S[3*])c1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1" ] }, "detailed_reactions": { "a": { "reactants": [ "CC(C)(C)C1=CC(=Cc2ccccc2)C=C(C(C)(C)C)C1=O", "Cc1ccc(S)cc1" ], "products": [ "Cc1ccc(SC(c2ccccc2)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)cc1" ] }, "b": { "reactants": [ "CC(C)(C)C1=CC(=Cc2ccc(C)cc2)C=C(C(C)(C)C)C1=O", "Cc1ccc(S)cc1" ], "products": [ "Cc1ccc(SC(c2ccc(C)cc2)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)cc1" ] }, "c": { "reactants": [ "CC(C)(C)C1=CC(=Cc2ccc(OC)cc2)C=C(C(C)(C)C)C1=O", "Cc1ccc(S)cc1" ], "products": [ "Cc1ccc(SC(c2ccc(OC)cc2)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)cc1" ] }, "d": { "reactants": [ "CC(C)(C)C1=CC(=Cc2ccc(Br)cc2)C=C(C(C)(C)C)C1=O", "Cc1ccc(S)cc1" ], "products": [ "Cc1ccc(SC(c2ccc(Br)cc2)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)cc1" ] }, "e": { "reactants": [ "CC(C)(C)C1=CC(=Cc2ccc(OC(F)(F)F)cc2)C=C(C(C)(C)C)C1=O", "Cc1ccc(S)cc1" ], "products": [ "Cc1ccc(SC(c2ccc(OC(F)(F)F)cc2)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)cc1" ] }, "f": { "reactants": [ "Cc1cccc(C=C2C=C(C(C)(C)C)C(=O)C(C(C)(C)C)=C2)c1", "Cc1ccc(S)cc1" ], "products": [ "Cc1ccc(SC(c2cccc(C)c2)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)cc1" ] }, "g": { "reactants": [ "Cc1cccc(C=C2C=C(C(C)(C)C)C(=O)C(C(C)(C)C)=C2)c1", "COc1ccc(S)cc1" ], "products": [ "Cc1ccc(SC(c2cccc(OC)c2)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)cc1" ] }, "h": { "reactants": [ "Cc1cccc(C=C2C=C(C(C)(C)C)C(=O)C(C(C)(C)C)=C2)c1", "Clc1ccc(S)cc1" ], "products": [ "Cc1ccc(SC(c2cccc(Cl)c2)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)cc1" ] }, "i": { "reactants": [ "COc1ccccc1C=C1C=C(C(C)(C)C)C(=O)C(C(C)(C)C)=C1", "Cc1ccc(S)cc1" ], "products": [ "COc1ccccc1C(Sc1ccc(C)cc1)c1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1" ] }, "j": { "reactants": [ "Fc1ccccc1C=C1C=C(C(C)(C)C)C(=O)C(C(C)(C)C)=C1", "Cc1ccc(S)cc1" ], "products": [ "Fc1ccccc1C(Sc1ccc(C)cc1)c1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1" ] }, "k": { "reactants": [ "Brc1ccccc1C=C1C=C(C(C)(C)C)C(=O)C(C(C)(C)C)=C1", "Cc1ccc(S)cc1" ], "products": [ "Brc1ccccc1C(Sc1ccc(C)cc1)c1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1" ] }, "l": { "reactants": [ "FC(F)(F)c1ccccc1C=C1C=C(C(C)(C)C)C(=O)C(C(C)(C)C)=C1", "Cc1ccc(S)cc1" ], "products": [ "FC(F)(F)c1ccccc1C(Sc1ccc(C)cc1)c1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1" ] }, "m": { "reactants": [ "CC(C)(C)C1=CC(=Cc2cccnc2)C=C(C(C)(C)C)C1=O", "Cc1ccc(S)cc1" ], "products": [ "Cc1ccc(SC(c2cccnc2)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)cc1" ] }, "n": { "reactants": [ "CC(C)(C)C1=CC(=Cc2ccc3ccccc3c2)C=C(C(C)(C)C)C1=O", "Cc1ccc(S)cc1" ], "products": [ "Cc1ccc(SC(c2ccc3ccccc3c2)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)cc1" ] }, "o": { "reactants": [ "CC(C)(C)C1=CC(=Cc2ccccc2)C=C(C(C)(C)C)C1=O", "COc1ccc(S)cc1" ], "products": [ "COc1ccc(SC(c2ccccc2)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)cc1" ] }, "p": { "reactants": [ "CC(C)(C)C1=CC(=Cc2ccccc2)C=C(C(C)(C)C)C1=O", "Clc1ccc(S)cc1" ], "products": [ "Clc1ccc(SC(c2ccccc2)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)cc1" ] }, "q": { "reactants": [ "CC(C)(C)C1=CC(=Cc2ccccc2)C=C(C(C)(C)C)C1=O", "Brc1ccc(S)cc1" ], "products": [ "Brc1ccc(SC(c2ccccc2)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)cc1" ] }, "r": { "reactants": [ "CC(C)(C)C1=CC(=Cc2ccccc2)C=C(C(C)(C)C)C1=O", "Cc1cc(S)ccc1" ], "products": [ "Cc1cc(SC(c2ccccc2)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)ccc1" ] }, "s": { "reactants": [ "CC(C)(C)C1=CC(=Cc2ccccc2)C=C(C(C)(C)C)C1=O", "Fc1cc(S)ccc1" ], "products": [ "Fc1cc(SC(c2ccccc2)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)ccc1" ] }, "t": { "reactants": [ "CC(C)(C)C1=CC(=Cc2ccccc2)C=C(C(C)(C)C)C1=O", "COc1c(S)cccc1" ], "products": [ "COc1c(SC(c2ccccc2)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)cccc1" ] }, "u": { "reactants": [ "CC(C)(C)C1=CC(=Cc2ccccc2)C=C(C(C)(C)C)C1=O", "Clc1c(S)cccc1" ], "products": [ "Clc1c(SC(c2ccccc2)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)cccc1" ] }, "v": { "reactants": [ "CC(C)(C)C1=CC(=Cc2ccccc2)C=C(C(C)(C)C)C1=O", "FC(F)(F)c1c(S)cccc1" ], "products": [ "FC(F)(F)c1c(SC(c2ccccc2)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)cccc1" ] }, "w": { "reactants": [ "CC(C)(C)C1=CC(=Cc2ccccc2)C=C(C(C)(C)C)C1=O", "Sc1cc2ccccc2cc1" ], "products": [ "CC(C)(C)c1cc(C(Sc2cc3ccccc3cc2)c2ccccc2)cc(C(C)(C)C)c1O" ] }, "x": { "reactants": [ "CC(C)(C)C1=CC(=Cc2ccccc2)C=C(C(C)(C)C)C1=O", "SCC(=O)OCC" ], "products": [ "CC(C)(C)c1cc(C(SCC(=O)OCC)c2ccccc2)cc(C(C)(C)C)c1O" ] }, "y": { "reactants": [ "CC(C)(C)C1=CC(=Cc2ccccc2)C=C(C(C)(C)C)C1=O", "O=C(CS)c1ccccc1" ], "products": [ "CC(C)(C)c1cc(C(SCC(=O)c2ccccc2)c2ccccc2)cc(C(C)(C)C)c1O" ] }, "z": { "reactants": [ "CC(C)(C)C1=CC(=Cc2ccccc2)C=C(C(C)(C)C)C1=O", "SCCCC" ], "products": [ "CC(C)(C)c1cc(C(SCCCC)c2ccccc2)cc(C(C)(C)C)c1O" ] } } }, { "file_name": "ajoc.202200438 example 2.png", "reaction_template": { "reactants": [ "[2*]C(=O)/C=C/[3*]", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "[2*]C(=O)[C@H]1[C@H]([3*])C(C(F)F)=NN1c1ccccc1" ] }, "detailed_reactions": { "ba": { "reactants": [ "Cc1ccc(C(=O)C=Cc2ccccc2)cc1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "Cc1ccc(C(=O)[C@H]2[C@H](c3ccccc3)C(C(F)F)=NN2c2ccccc2)cc1" ] }, "ca": { "reactants": [ "COc1ccc(C(=O)C=Cc2ccccc2)cc1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "COc1ccc(C(=O)[C@H]2[C@H](c3ccccc3)C(C(F)F)=NN2c2ccccc2)cc1" ] }, "da": { "reactants": [ "Nc1ccc(C(=O)C=Cc2ccccc2)cc1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "Nc1ccc(C(=O)[C@H]2[C@H](c3ccccc3)C(C(F)F)=NN2c2ccccc2)cc1" ] }, "ea": { "reactants": [ "O=C(C=Cc1ccccc1)c1ccc2c(c1)OCO2", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "O=C(c1ccc2c(c1)OCO2)[C@H]1[C@H](c2ccccc2)C(C(F)F)=NN1c1ccccc1" ] }, "fa": { "reactants": [ "Fc1ccc(C(=O)C=Cc2ccccc2)cc1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "Fc1ccc(C(=O)[C@H]2[C@H](c3ccccc3)C(C(F)F)=NN2c2ccccc2)cc1" ] }, "ga": { "reactants": [ "Brc1ccc(C(=O)C=Cc2ccccc2)cc1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "Brc1ccc(C(=O)[C@H]2[C@H](c3ccccc3)C(C(F)F)=NN2c2ccccc2)cc1" ] }, "ha": { "reactants": [ "[O-][N+](=O)c1ccc(C(=O)C=Cc2ccccc2)cc1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "[O-][N+](=O)c1ccc(C(=O)[C@H]2[C@H](c3ccccc3)C(C(F)F)=NN2c2ccccc2)cc1" ] }, "ia": { "reactants": [ "O=C(C=Cc1ccccc1)c1ccc2ccccc2c1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "O=C(c1ccc2ccccc2c1)[C@H]1[C@H](c2ccccc2)C(C(F)F)=NN1c1ccccc1" ] }, "ja": { "reactants": [ "CC(=O)C=Cc1ccccc1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "CC(=O)[C@H]1[C@H](c2ccccc2)C(C(F)F)=NN1c1ccccc1" ] }, "ka": { "reactants": [ "CC(C)(C)C(=O)C=Cc1ccccc1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "CC(C)(C)C(=O)[C@H]1[C@H](c2ccccc2)C(C(F)F)=NN1c1ccccc1" ] }, "la": { "reactants": [ "O=C(C=Cc1ccccc1)C1CCCCC1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "O=C(C1CCCCC1)[C@H]1[C@H](c2ccccc2)C(C(F)F)=NN1c1ccccc1" ] }, "ma": { "reactants": [ "Cc1c(C=CC(=O)c2ccccc2)cccc1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "Cc1c([C@@H]2C(C(F)F)=NN(c3ccccc3)[C@H]2C(=O)c2ccccc2)cccc1" ] }, "na": { "reactants": [ "Cc1cc(C=CC(=O)c2ccccc2)ccc1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "Cc1cc([C@@H]2C(C(F)F)=NN(c3ccccc3)[C@H]2C(=O)c2ccccc2)ccc1" ] }, "oa": { "reactants": [ "Cc1ccc(C=CC(=O)c2ccccc2)cc1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "Cc1ccc([C@@H]2C(C(F)F)=NN(c3ccccc3)[C@H]2C(=O)c2ccccc2)cc1" ] }, "pa": { "reactants": [ "COc1ccc(C=CC(=O)c2ccccc2)cc1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "COc1ccc([C@@H]2C(C(F)F)=NN(c3ccccc3)[C@H]2C(=O)c2ccccc2)cc1" ] }, "qa": { "reactants": [ "Fc1ccc(C=CC(=O)c2ccccc2)cc1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "Fc1ccc([C@@H]2C(C(F)F)=NN(c3ccccc3)[C@H]2C(=O)c2ccccc2)cc1" ] }, "ra": { "reactants": [ "O=C(C=Cc1ccc(Br)cc1)c1ccccc1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "O=C(c1ccccc1)[C@H]1[C@H](c2ccc(Br)cc2)C(C(F)F)=NN1c1ccccc1" ] }, "sa": { "reactants": [ "O=C(C=Cc1ccc([N+](=O)[O-])cc1)c1ccccc1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "O=C(c1ccccc1)[C@H]1[C@H](c2ccc([N+](=O)[O-])cc2)C(C(F)F)=NN1c1ccccc1" ] }, "ta": { "reactants": [ "O=C(C=Cc1ccco1)c1ccccc1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "O=C(c1ccccc1)[C@H]1[C@H](c2ccco2)C(C(F)F)=NN1c1ccccc1" ] }, "ua": { "reactants": [ "O=C(C=Cc1cccs1)c1ccccc1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "O=C(c1ccccc1)[C@H]1[C@H](c2cccs2)C(C(F)F)=NN1c1ccccc1" ] }, "va": { "reactants": [ "O=C(C=Cc1ccc[nH]1)c1ccccc1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "O=C(c1ccccc1)[C@H]1[C@H](c2ccc[nH]2)C(C(F)F)=NN1c1ccccc1" ] }, "wa": { "reactants": [ "CC=CC(=O)c1ccccc1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "C[C@@H]1C(C(F)F)=NN(c2ccccc2)[C@H]1C(=O)c1ccccc1" ] }, "xa": { "reactants": [ "CC(C)C=CC(=O)c1ccccc1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "CC(C)[C@@H]1C(C(F)F)=NN(c2ccccc2)[C@H]1C(=O)c1ccccc1" ] } } }, { "file_name": "ajoc.202200438 example 3.png", "reaction_template": { "reactants": [ "*C(=O)/C=C/[4*]", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "*C(=O)[C@H]1[C@H]([4*])C(C(F)F)=NN1c1ccccc1" ] }, "detailed_reactions": { "a": { "reactants": [ "COC(=O)/C=C", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "COC(=O)[C@H]1[C@H]C(C(F)F)=NN1c1ccccc1" ] }, "b": { "reactants": [ "CCOC(=O)/C=C", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "CCOC(=O)[C@H]1[C@H]C(C(F)F)=NN1c1ccccc1" ] }, "c": { "reactants": [ "COC(=O)/C=C/C", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "COC(=O)[C@H]1[C@H](C)C(C(F)F)=NN1c1ccccc1" ] }, "d": { "reactants": [ "COC(=O)/C=C/CCC", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "COC(=O)[C@H]1[C@H](CCC)C(C(F)F)=NN1c1ccccc1" ] }, "e": { "reactants": [ "COC(=O)/C=C/c1ccccc1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "COC(=O)[C@H]1[C@H](c2ccccc2)C(C(F)F)=NN1c1ccccc1" ] }, "f": { "reactants": [ "CCOC(=O)/C=C/c1ccc(C)cc1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "CCOC(=O)[C@H]1[C@H](c2ccc(C)cc2)C(C(F)F)=NN1c1ccccc1" ] }, "g": { "reactants": [ "COC(=O)/C=C/c1ccc(Cl)cc1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "COC(=O)[C@H]1[C@H](c2ccc(Cl)cc2)C(C(F)F)=NN1c1ccccc1" ] }, "h": { "reactants": [ "COC(=O)/C=C/C(=O)OC", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "COC(=O)[C@H]1[C@H](C(=O)OC)C(C(F)F)=NN1c1ccccc1" ] }, "i": { "reactants": [ "NC(=O)/C=C", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "NC(=O)[C@H]1[C@H]C(C(F)F)=NN1c1ccccc1" ] }, "j": { "reactants": [ "CN(C)C(=O)/C=C", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "CN(C)C(=O)[C@H]1[C@H]C(C(F)F)=NN1c1ccccc1" ] }, "k": { "reactants": [ "c1ccccc1CNC(=O)/C=C", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "c1ccccc1CNC(=O)[C@H]1[C@H]C(C(F)F)=NN1c1ccccc1" ] }, "l": { "reactants": [ "c1ccccc1-NC(=O)/C=C", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "c1ccccc1-NC(=O)[C@H]1[C@H]C(C(F)F)=NN1c1ccccc1" ] }, "m": { "reactants": [ "CC=CC(N)=O", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "C[C@@H]1C(C(F)F)=NN(c2ccccc2)[C@H]1C(N)=O" ] }, "n": { "reactants": [ "NC(=O)/C=C/c1ccccc1", "FC(F)/C(Br)=N/Nc1ccccc1" ], "products": [ "NC(=O)[C@H]1[C@H](c2ccccc2)C(C(F)F)=NN1c1ccccc1" ] } } }, { "file_name": "ajoc.202200438 example 4.png", "reaction_template": { "reactants": [ "[5*]C=C[N+](=O)[O-]", "FC(F)/C(Br)=N/N[1*]" ], "products": [ "[5*]c1cn([1*])nc1C(F)F" ] }, "detailed_reactions": { "a": { "reactants": [ "c1ccccc1-C=C[N+](=O)[O-]", "FC(F)/C(Br)=N/N-c1ccccc1" ], "products": [ "c1ccccc1-c1cn(-c2ccccc2)nc1C(F)F" ] }, "b": { "reactants": [ "c1cc(C)ccc1-C=C[N+](=O)[O-]", "FC(F)/C(Br)=N/N-c1ccccc1" ], "products": [ "c1cc(C)ccc1-c1cn(-c2ccccc2)nc1C(F)F" ] }, "c": { "reactants": [ "c1cc(OC)ccc1-C=C[N+](=O)[O-]", "FC(F)/C(Br)=N/N-c1ccccc1" ], "products": [ "c1cc(OC)ccc1-c1cn(-c2ccccc2)nc1C(F)F" ] }, "d": { "reactants": [ "c1cc(Cl)ccc1-C=C[N+](=O)[O-]", "FC(F)/C(Br)=N/N-c1ccccc1" ], "products": [ "c1cc(Cl)ccc1-c1cn(-c2ccccc2)nc1C(F)F" ] }, "e": { "reactants": [ "c1cc(Br)ccc1-C=C[N+](=O)[O-]", "FC(F)/C(Br)=N/N-c1ccccc1" ], "products": [ "c1cc(Br)ccc1-c1cn(-c2ccccc2)nc1C(F)F" ] }, "f": { "reactants": [ "c1cc(C(=O)OC)ccc1-C=C[N+](=O)[O-]", "FC(F)/C(Br)=N/N-c1ccccc1" ], "products": [ "c1cc(C(=O)OC)ccc1-c1cn(-c2ccccc2)nc1C(F)F" ] }, "g": { "reactants": [ "c1c2ccccc2ccc1-C=C[N+](=O)[O-]", "FC(F)/C(Br)=N/N-c1ccccc1" ], "products": [ "c1c2ccccc2ccc1-c1cn(-c2ccccc2)nc1C(F)F" ] }, "h": { "reactants": [ "c1ccccc1-C=C[N+](=O)[O-]", "FC(F)/C(Br)=N/N-c1ccc(C)cc1" ], "products": [ "c1ccccc1-c1cn(-c2ccc(C)cc2)nc1C(F)F" ] }, "i": { "reactants": [ "c1ccccc1-C=C[N+](=O)[O-]", "FC(F)/C(Br)=N/N-c1ccc(Br)cc1" ], "products": [ "c1ccccc1-c1cn(-c2ccc(Br)cc2)nc1C(F)F" ] }, "j": { "reactants": [ "c1ccccc1-C=C[N+](=O)[O-]", "FC(F)/C(Br)=N/N-c1ccc(C(=O)OC)cc1" ], "products": [ "c1ccccc1-c1cn(-c2ccc(C(=O)OC)cc2)nc1C(F)F" ] }, "k": { "reactants": [ "c1cc(OC)ccc1-C=C[N+](=O)[O-]", "FC(F)/C(Br)=N/N-c1ccc(F)cc1" ], "products": [ "c1cc(OC)ccc1-c1cn(-c2ccc(F)cc2)nc1C(F)F" ] }, "l": { "reactants": [ "c1ccccc1-C=C[N+](=O)[O-]", "FC(F)/C(Br)=N/N-c1ccncc1" ], "products": [ "c1ccccc1-c1cn(-c2ccncc2)nc1C(F)F" ] } } }, { "file_name": "ajoc.202200438 example 1.png", "reaction_template": { "reactants": [ "O=C(C=Cc1ccccc1)c1ccccc1", "FC(F)/C(Br)=N/N[1*]" ], "products": [ "[1*]N1N=C(C(F)F)[C@@H](c2ccccc2)[C@@H]1C(=O)c1ccccc1" ] }, "detailed_reactions": { "ab": { "reactants": [ "O=C(C=Cc1ccccc1)c1ccccc1", "FC(F)/C(Br)=N/N-c1c(C)cccc1" ], "products": [ "c1cccc(C)c1-N1N=C(C(F)F)[C@@H](c2ccccc2)[C@@H]1C(=O)c1ccccc1" ] }, "ac": { "reactants": [ "O=C(C=Cc1ccccc1)c1ccccc1", "FC(F)/C(Br)=N/N-c1cc(C)ccc1" ], "products": [ "c1ccc(C)cc1-N1N=C(C(F)F)[C@@H](c2ccccc2)[C@@H]1C(=O)c1ccccc1" ] }, "ad": { "reactants": [ "O=C(C=Cc1ccccc1)c1ccccc1", "FC(F)/C(Br)=N/N-c1ccc(C)cc1" ], "products": [ "c1cc(C)ccc1-N1N=C(C(F)F)[C@@H](c2ccccc2)[C@@H]1C(=O)c1ccccc1" ] }, "ae": { "reactants": [ "O=C(C=Cc1ccccc1)c1ccccc1", "FC(F)/C(Br)=N/N-c1ccc(CC)cc1" ], "products": [ "c1cc(CC)ccc1-N1N=C(C(F)F)[C@@H](c2ccccc2)[C@@H]1C(=O)c1ccccc1" ] }, "af": { "reactants": [ "O=C(C=Cc1ccccc1)c1ccccc1", "FC(F)/C(Br)=N/N-c1ccc(C(C)(C)C)cc1" ], "products": [ "c1cc(C(C)(C)C)ccc1-N1N=C(C(F)F)[C@@H](c2ccccc2)[C@@H]1C(=O)c1ccccc1" ] }, "ag": { "reactants": [ "O=C(C=Cc1ccccc1)c1ccccc1", "FC(F)/C(Br)=N/N-c1ccc(F)cc1" ], "products": [ "c1cc(F)ccc1-N1N=C(C(F)F)[C@@H](c2ccccc2)[C@@H]1C(=O)c1ccccc1" ] }, "ah": { "reactants": [ "O=C(C=Cc1ccccc1)c1ccccc1", "FC(F)/C(Br)=N/N-c1c(Br)cccc1" ], "products": [ "c1cccc(Br)c1-N1N=C(C(F)F)[C@@H](c2ccccc2)[C@@H]1C(=O)c1ccccc1" ] }, "ai": { "reactants": [ "O=C(C=Cc1ccccc1)c1ccccc1", "FC(F)/C(Br)=N/N-c1cc(Br)ccc1" ], "products": [ "c1ccc(Br)cc1-N1N=C(C(F)F)[C@@H](c2ccccc2)[C@@H]1C(=O)c1ccccc1" ] }, "aj": { "reactants": [ "O=C(C=Cc1ccccc1)c1ccccc1", "FC(F)/C(Br)=N/N-c1ccc(Br)cc1" ], "products": [ "c1cc(Br)ccc1-N1N=C(C(F)F)[C@@H](c2ccccc2)[C@@H]1C(=O)c1ccccc1" ] }, "ak": { "reactants": [ "O=C(C=Cc1ccccc1)c1ccccc1", "FC(F)/C(Br)=N/N-c1ccc(C(F)(F)F)cc1" ], "products": [ "c1cc(C(F)(F)F)ccc1-N1N=C(C(F)F)[C@@H](c2ccccc2)[C@@H]1C(=O)c1ccccc1" ] }, "al": { "reactants": [ "O=C(C=Cc1ccccc1)c1ccccc1", "FC(F)/C(Br)=N/N-c1ccc2ccccc2c1" ], "products": [ "c1cc2ccccc2cc1-N1N=C(C(F)F)[C@@H](c2ccccc2)[C@@H]1C(=O)c1ccccc1" ] }, "am": { "reactants": [ "O=C(C=Cc1ccccc1)c1ccccc1", "FC(F)/C(Br)=N/N-c1ccncc1" ], "products": [ "c1cnccc1-N1N=C(C(F)F)[C@@H](c2ccccc2)[C@@H]1C(=O)c1ccccc1" ] } } }, { "file_name": "ejoc.202300573 example 1.png", "reaction_template": { "reactants": [ "*C(=COCC)C(=O)C#C[Si](C)(C)C" ], "products": [ "*c1coc([Si](C)(C)C)cc1=O" ] }, "detailed_reactions": { "a": { "reactants": [ "CCOC=C(C(=O)C#C[Si](C)(C)C)c1ccccc1" ], "products": [ "C[Si](C)(C)c1cc(=O)c(-c2ccccc2)co1" ] }, "b": { "reactants": [ "CCOC=C(C(=O)C#C[Si](C)(C)C)c1ccc(C)cc1" ], "products": [ "Cc1ccc(-c2coc([Si](C)(C)C)cc2=O)cc1" ] }, "c": { "reactants": [ "CCOC=C(C(=O)C#C[Si](C)(C)C)c1ccc(OC)cc1" ], "products": [ "COc1ccc(-c2coc([Si](C)(C)C)cc2=O)cc1" ] }, "d": { "reactants": [ "CCOC=C(C(=O)C#C[Si](C)(C)C)c1ccc(Cl)cc1" ], "products": [ "C[Si](C)(C)c1cc(=O)c(-c2ccc(Cl)cc2)co1" ] }, "e": { "reactants": [ "CCOC=C(C(=O)C#C[Si](C)(C)C)c1ccc(F)cc1" ], "products": [ "C[Si](C)(C)c1cc(=O)c(-c2ccc(F)cc2)co1" ] }, "f": { "reactants": [ "CCOC=C(C(=O)C#C[Si](C)(C)C)c1ccc([N+](=O)[O-])cc1" ], "products": [ "C[Si](C)(C)c1cc(=O)c(-c2ccc([N+](=O)[O-])cc2)co1" ] }, "g": { "reactants": [ "CCOC=C(C(=O)C#C[Si](C)(C)C)c1ccccc1Cl" ], "products": [ "C[Si](C)(C)c1cc(=O)c(-c2ccccc2Cl)co1" ] }, "h": { "reactants": [ "CCOC=C(C(=O)C#C[Si](C)(C)C)c1ccccc1OC" ], "products": [ "COc1ccccc1-c1coc([Si](C)(C)C)cc1=O" ] }, "i": { "reactants": [ "CCOC=C(C(=O)C#C[Si](C)(C)C)c1cc(C)ccc1C" ], "products": [ "Cc1ccc(C)c(-c2coc([Si](C)(C)C)cc2=O)c1" ] }, "j": { "reactants": [ "CCOC=C(C(=O)C#C[Si](C)(C)C)c1ccc(C)cc1C" ], "products": [ "Cc1ccc(-c2coc([Si](C)(C)C)cc2=O)c(C)c1" ] }, "k": { "reactants": [ "CCOC=C(C(=O)C#C[Si](C)(C)C)c1ccc([N+](=O)[O-])cc1[N+](=O)[O-]" ], "products": [ "C[Si](C)(C)c1cc(=O)c(-c2ccc([N+](=O)[O-])cc2[N+](=O)[O-])co1" ] }, "l": { "reactants": [ "CCOC=C(C(=O)C#C[Si](C)(C)C)c1ccc(Cl)c(Cl)c1" ], "products": [ "C[Si](C)(C)c1cc(=O)c(-c2ccc(Cl)c(Cl)c2)co1" ] }, "m": { "reactants": [ "CCOC=C(C(=O)C#C[Si](C)(C)C)c1cccc2ccccc12" ], "products": [ "C[Si](C)(C)c1cc(=O)c(-c2cccc3ccccc23)co1" ] }, "n": { "reactants": [ "CCOC=C(C(=O)C#C[Si](C)(C)C)c1ccc2ccccc2c1" ], "products": [ "C[Si](C)(C)c1cc(=O)c(-c2ccc3ccccc3c2)co1" ] } } }, { "file_name": "ejoc.202300531 example 1.png", "reaction_template": { "reactants": [ "[H]c1c(-c2nc3ccccc3[nH]2)c(=O)oc2ccccc12", "[2*]OC(=O)C=C" ], "products": [ "[2*]OC(=O)c1cc2c3ccccc3oc(=O)c2c2nc3ccccc3n12" ] }, "detailed_reactions": { "aa": { "reactants": [ "O=c1oc2ccccc2cc1-c1nc2ccccc2[nH]1", "C=CC(=O)OC" ], "products": [ "COC(=O)c1cc2c3ccccc3oc(=O)c2c2nc3ccccc3n12" ] }, "ab": { "reactants": [ "O=c1oc2ccccc2cc1-c1nc2ccccc2[nH]1", "C=CC(=O)OCC" ], "products": [ "CCOC(=O)c1cc2c3ccccc3oc(=O)c2c2nc3ccccc3n12" ] }, "ac": { "reactants": [ "O=c1oc2ccccc2cc1-c1nc2ccccc2[nH]1", "C=CC(=O)OC(C)(C)C" ], "products": [ "CC(C)(C)OC(=O)c1cc2c3ccccc3oc(=O)c2c2nc3ccccc3n12" ] }, "ad": { "reactants": [ "O=c1oc2ccccc2cc1-c1nc2ccccc2[nH]1", "C=CC(=O)OCCCC" ], "products": [ "CCCCOC(=O)c1cc2c3ccccc3oc(=O)c2c2nc3ccccc3n12" ] }, "ae": { "reactants": [ "O=c1oc2ccccc2cc1-c1nc2ccccc2[nH]1", "C=CC(=O)OCC(CC)CCCC" ], "products": [ "CCCCC(CC)COC(=O)c1cc2c3ccccc3oc(=O)c2c2nc3ccccc3n12" ] }, "af": { "reactants": [ "O=c1oc2ccccc2cc1-c1nc2ccccc2[nH]1", "C=CC(=O)C" ], "products": [ "CC(=O)c1cc2c3ccccc3oc(=O)c2c2nc3ccccc3n12" ] }, "ag": { "reactants": [ "O=c1oc2ccccc2cc1-c1nc2ccccc2[nH]1", "C=CS(=O)(=O)-c1ccccc1" ], "products": [ "O=c1oc2ccccc2c2cc(S(=O)(=O)c3ccccc3)n3c4ccccc4nc3c12" ] } } }, { "file_name": "ejoc.202300531 example 2.png", "reaction_template": { "reactants": [ "[1*]c1ccc2c([H])c(-c3nc4cc([3*])ccc4[nH]3)c(=O)oc2c1", "[2*]OC(=O)C=C" ], "products": [ "[2*]OC(=O)c1cc2c3ccc([1*])cc3oc(=O)c2c2nc3cc([3*])ccc3n12" ] }, "detailed_reactions": { "ba": { "reactants": [ "c1ccc2c([H])c(-c3nc4cc(C)ccc4[nH]3)c(=O)oc2c1", "[2*]OC(=O)C=C" ], "products": [ "[2*]OC(=O)c1cc2c3ccccc3oc(=O)c2c2nc3cc(C)ccc3n12" ] }, "ca": { "reactants": [ "c1ccc2c([H])c(-c3nc4cc([N+](=O)[O-])ccc4[nH]3)c(=O)oc2c1", "[2*]OC(=O)C=C" ], "products": [ "[2*]OC(=O)c1cc2c3ccccc3oc(=O)c2c2nc3cc([N+](=O)[O-])ccc3n12" ] }, "da": { "reactants": [ "c1ccc2c([H])c(-c3nc4cc(Br)ccc4[nH]3)c(=O)oc2c1", "[2*]OC(=O)C=C" ], "products": [ "[2*]OC(=O)c1cc2c3ccccc3oc(=O)c2c2nc3cc(Br)ccc3n12" ] }, "ea": { "reactants": [ "Brc1ccc2c([H])c(-c3nc4ccccc4[nH]3)c(=O)oc2c1", "[2*]OC(=O)C=C" ], "products": [ "[2*]OC(=O)c1cc2c3ccc(Br)cc3oc(=O)c2c2nc3ccccc3n12" ] }, "eb": { "reactants": [ "Brc1ccc2c([H])c(-c3nc4ccccc4[nH]3)c(=O)oc2c1", "[2*]OC(=O)C=C" ], "products": [ "[2*]OC(=O)c1cc2c3ccc(Br)cc3oc(=O)c2c2nc3ccccc3n12" ] }, "ec": { "reactants": [ "Brc1ccc2c([H])c(-c3nc4ccccc4[nH]3)c(=O)oc2c1", "[2*]OC(=O)C=C" ], "products": [ "[2*]OC(=O)c1cc2c3ccc(Br)cc3oc(=O)c2c2nc3ccccc3n12" ] }, "fa": { "reactants": [ "Clc1ccc2c([H])c(-c3nc4ccccc4[nH]3)c(=O)oc2c1", "[2*]OC(=O)C=C" ], "products": [ "[2*]OC(=O)c1cc2c3ccc(Cl)cc3oc(=O)c2c2nc3ccccc3n12" ] }, "fb": { "reactants": [ "Clc1ccc2c([H])c(-c3nc4ccccc4[nH]3)c(=O)oc2c1", "[2*]OC(=O)C=C" ], "products": [ "[2*]OC(=O)c1cc2c3ccc(Cl)cc3oc(=O)c2c2nc3ccccc3n12" ] }, "fc": { "reactants": [ "Clc1ccc2c([H])c(-c3nc4ccccc4[nH]3)c(=O)oc2c1", "[2*]OC(=O)C=C" ], "products": [ "[2*]OC(=O)c1cc2c3ccc(Cl)cc3oc(=O)c2c2nc3ccccc3n12" ] }, "ga": { "reactants": [ "COc1ccc2c([H])c(-c3nc4ccccc4[nH]3)c(=O)oc2c1", "[2*]OC(=O)C=C" ], "products": [ "[2*]OC(=O)c1cc2c3ccc(OC)cc3oc(=O)c2c2nc3ccccc3n12" ] }, "gb": { "reactants": [ "COc1ccc2c([H])c(-c3nc4ccccc4[nH]3)c(=O)oc2c1", "[2*]OC(=O)C=C" ], "products": [ "[2*]OC(=O)c1cc2c3ccc(OC)cc3oc(=O)c2c2nc3ccccc3n12" ] }, "gc": { "reactants": [ "COc1ccc2c([H])c(-c3nc4ccccc4[nH]3)c(=O)oc2c1", "[2*]OC(=O)C=C" ], "products": [ "[2*]OC(=O)c1cc2c3ccc(OC)cc3oc(=O)c2c2nc3ccccc3n12" ] }, "ha": { "reactants": [ "c1c3ccccc3c2c([H])c(-c3nc4ccccc4[nH]3)c(=O)oc2c1", "COC(=O)C=C" ], "products": [ "COC(=O)c1cc2c3c4ccccc4ccc3oc(=O)c2c2nc3ccccc3n12" ] }, "hb": { "reactants": [ "c1c3ccccc3c2c([H])c(-c3nc4ccccc4[nH]3)c(=O)oc2c1", "CCOC(=O)C=C" ], "products": [ "CCOC(=O)c1cc2c3c4ccccc4ccc3oc(=O)c2c2nc3ccccc3n12" ] }, "hc": { "reactants": [ "c1c3ccccc3c2c([H])c(-c3nc4ccccc4[nH]3)c(=O)oc2c1", "CC(C)(C)OC(=O)C=C" ], "products": [ "CC(C)(C)OC(=O)c1cc2c3c4ccccc4ccc3oc(=O)c2c2nc3ccccc3n12" ] } } } ]