Patent ID: 6593498
Filing Date: 2003-07-15
Classification: C07F

Abstract:
A method for forming a boratabenzene having formula X: the method comprising:1) reacting an alkynyl magnesium bromide having formula II: â€ƒwith a propargyl benzenesulfonate having formula III: â€ƒand with CuBr in a first chemically inert solvent to form a first solution containing a 1,4-pentadiyne having formula IV: 2) adding a second chemically inert solvent to the first solution to form a second solution of the 1,4-pentadiyne wherein the second solution has a greater volatility than the first solution; 3) distilling the second solution such that a third solution comprising the second solvent and the 1,4-pentadiyne is collected; 4) reacting the third solution with a tin dihydride having formula V: â€ƒto form a stannacyclohexa-2,5-diene having formula VI: 5) reacting the stannacyclohexa-2,5-diene with a boron halide having formula VII: BX3â€ƒâ€ƒ(VII) â€ƒto form a 1-haloboracyclohexa-2,5-diene having formula VIII: 6) reacting the reacting the 1-haloboracyclohexa-2,5-diene with an alkylating agent to from a boracyclohexa-2,5-diene having formula IX: 7) reacting the boracyclohexa-2,5-diene with a strong base to form the boratabenzene: wherein, R1 is hydrogen, a C1-10 alkyl group, a C6-10 aryl group, or a C7-15 aralkyl group; R2 is hydrogen, a C1-10 alkyl group, a C6-10 aryl group, or a C7-15 aralkyl group; R3 is a C1-10 alkyl group, a C6-10 aryl group, or a C7-15 aralkyl group; R4 is a C1-10 alkyl group, a C6-10 aryl group, or a C7-15 aralkyl group; R5 is a C1-10 alkyl group, a C6-10 aryl group, or a C7-15 aralkyl group; X is a halogen; and M+ is a metal cation.