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Timestamp: 2019-04-20 04:11:39+00:00

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Physical Data: mp. 108-110 °C (dec); 1H NMR d (C6D6) 2.55 ppm (C2H4).
Solubility: very sol benzene, toluene; sparingly sol ether, pentane.
Form Supplied in: yellow crystalline solid; not commercially available.
Purification: can be recrystallized from methanol at reduced temperatures.
Handling, Storage, and Precautions: is very air sensitive and should be stored under inert atmosphere, preferably in a dry box.
Ethylenebis(triphenylphosphine)nickel(0) has been used as an isomerization catalyst for the ring expansion of vinylcyclobutenes to cyclohexadienes.2,11 It also promotes the dechlorination of 1,2-dichlorides to the corresponding cyclobutenes. The reactions can be carried out independently, or direct conversion of the dichloride to the cyclohexadiene is also possible (eq 3). Conditions under which these transformations are carried out include thermolysis followed by oxidation of the resulting Ni0 alkene complex to NiI and subsequent ring expansion, or preoxidation of the catalyst to NiI. Yields range from 40-50%. The presence of electron-withdrawing substituents on the cyclobutene system are required, whereas substitution on the vinyl group effectively lowers yields.
Reaction with Alkenic and Allenic Compounds.
The catalyst can be utilized with a number of alkenes under either thermal or photochemical conditions to produce cyclobutane and other dimerized products. For example, irradiation of a toluene solution of 1,7-octadiene with ethylenebis(triphenylphosphine)nickel(0) followed by air oxidation yields stereospecifically trans-bicyclo[4.2.0]octane accompanied by oligomers (eq 6).4 The reaction also works intermolecularly with monosubstituted alkenes, yielding the corresponding 1,2-trans-cyclobutanes (eq 7).
The catalyst (2.5 mol %) also reacts with allene at elevated temperatures to yield a mixture of the trimer, tetramer, pentamer, and higher oligomers (eq 12).23 The related complex Bis(1,5-cyclooctadiene)nickel(0) also promotes a similar reaction.
1. Jolly, P. W. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed.; Pergamon: 1982; Vol. 6, pp 101-143.
2. Choi, H.; Hershberger, J. W.; Pinhas, A. R.; Ho, D. M. OM 1991, 10, 2930.
3. Hipler, B.; Uhlig, E. ZC 1986, 26, 260.
4. Miyashita, A.; Ikezu, S.; Nohira, H. CL 1985, 1235.
5. Grubbs, R. H.; Miyashita, A. JOM 1978, 161, 371.
6. Davidson, J. G.; Barefield, E. K.; Derveer, D. G. V. OM 1985, 4, 1178.
7. Miller, R. G.; Fahey, D. R.; Golden, H. J.; Satek, L. C. JOM 1974, 82, 127.
8. Wilke, G.; Herrmann, G. AG(E) 1962, 1, 549.
9. Greaves, E. O.; Lock, C. J. L.; Maitlis, P. M. CJC 1968, 46, 3879.
10. Giannoccaro, P.; Sacco, A.; Vasapollo, G. ICA 1979, 37, L455.
11. Choi, H.; Pinhas, A. R. OM 1992, 11, 442.
12. Bartsch, E.; Dinjus, E.; Uhlig, E. ZC 1975, 15, 317.
13. Bartsch, E.; Dinjus, E.; Fischer, R.; Uhlig, E. Z. Anorg. Allg. Chem. 1977, 433, 5.
14. Uhlig, E.; Hipler, B. TL 1984, 25, 5871.
15. Bockelheide, V. Top. Curr. Chem. 1983, 113, 87.
16. Grubbs, R. H.; Miyashita, A.; Liu, M.-I. M.; Burk, P. L. JACS 1977, 99, 3863.
17. Grubbs, R. H.; Miyashita, A. JACS 1978, 100, 7416.
18. Furman, D. B.; Volchkov, N. V.; Isaeva, L. S.; Morozova, L. N.; Kravtsov, D. N.; Bragin, O. V. BAU 1989, 37, 2220.
19. Peganova, T. A.; Petrovskii, P. V.; Isaeva, L. S.; Kravstov, D. N.; Furman, D. B.; Kudryashev, A. V.; Ivanov, A. O.; Zotova, S. V.; Bragin, O. V. JOM 1985, 282, 283.
20. Furman, D. B.; Rudashevskaya, T. Y.; Kudryashev, A. V.; Ivanov, A. O.; Isaeva, L. S.; Morozova, L. N.; Peganova, T. A.; Bogdanov, V. S.; Kravtsov, D. N.; Bragin, O. V. IZV 1990, 345.
21. Ascenso, J. R.; Carrondo, M. A. A. F. de C. T.; Dias, A. R.; Gomes, P. T.; Piedade, M. F. M.; Romao, C. C. Polyhedron 1989, 8, 2449.
22. Miller, R. G.; Pinke, P. A.; Stauffer, R. D.; Golden, H. J.; Baker, D. J. JACS 1974, 96, 4211.
23. Otsuka, S.; Tani, K.; Yamagata, T. JCS(D) 1973, 2491.
24. Hoberg, H.; Summermann, K.; Milchereit, A. JOM 1985, 288, 237.

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