Olefin-olefin reactions mediated by Lewis acids may afford cyclopropanes rather than cyclobutanes: A mechanistic study of cyclopropane formation using a 1-seleno-2-silylethene

Journal of the Chemical Society, Perkin Transactions 2

Volumn , Issue 2, 2001, Pages 164-173

  Yamazaki, Shoko ^a   Yamabe, Shinichi ^a  

^a NARA UNIVERSITY OF EDUCATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; COMPLEXATION; MOLECULAR STRUCTURE; ORGANIC ACIDS; PARAFFINS; PROBABILITY DENSITY FUNCTION;

DENSITY FUNCTIONAL THEORY (DFT);

OLEFINS;

EID: 0035770701     PISSN: 14701820     EISSN: None     Source Type: Journal    
DOI: 10.1039/b007390n     Document Type: Article

References (29)

1. R. B. Woodward and R. Hoffmann, The Conservation of Orbital Symmetry, Academic Press, New York, 1970.
2. R. Huisgen, Acc. Chem. Res., 1977, 10, 117;
3. R. Huisgen, Ace. Chem. Res., 1977, 10, 199.
4. (a) T. Okuyama, M. Nakada, K. Toyoshima and T. Fueno, J. Org. Chem., 1978, 43, 4546;
5. (b) T. Takeda, T. Fujii, K. Morita and T. Fujiwara, Chem. Lett., 1986, 1311;
6. K. Narasaka, Y. Hayashi, H. Shimadzu and S. Niihara, J. Am. Chem. Soc., 1992, 114, 8869;
7. W. Srisiri, A. B. Padias and H. K. Hall, Jr., J. Org. Chem., 1994, 59, 5424;
8. (e) R. D. Clark and K. G. Untch, J. Org. Chem., 1979, 44, 248;
9. R. D. Clark and R. G. Untch, J. Org. Chem., 1979, 44, 253;
10. (f) M. R. Baar, P. Ballesteros and B. W. Roberts, Tetrahedron Lett., 1986, 27, 2083.
11. K. Narasaka, K. Soai, Y. Aikawa and T. Mukaiyama, Bull. Chem. Soc. Jpn., 1976, 49, 779.
12. (a) H. M. R. Hoffmann, Angew. Chem., Int. Ed. Engl., 1969, 8, 556;
13. (b) B. B. Snider, Acc. Chem. Res., 1980, 13, 426;
14. K. Mikami and M. Shimizu, Chem. Rev., 1992, 92, 1021.
15. (a) D. L. Boger, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 5, pp. 451-512;
16. (b) D. A. Evans and J. S. Johnson, J. Am. Chem. Soc., 1998, 120, 4895 and references therein.
17. (a) A. G. Brook and A. R. Bassindale, in Rearrangements in Ground and Excited States, ed. P. de Mayo, Academic Press, New York, 1980, vol. II, pp. 190-192;
18. (b) J. S. Panek, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Flemine, Pergamon Press, Oxford, 1991, vol. 1, pp. 579-627;
19. H.-J. Knölker, J. Prakt. Chem., 1997, 339, 304.
20. (a) B. N. Solomonov, I. A. Arkhireeva and A. I. Kohovalov, Zh. Org. Khim., 1980, 16, 1670;
21. (b) S. Yamazaki, H. Fujitsuka, S. Yamabe and H. Tamura, J. Org. Chem., 1992, 57, 5610.
22. (a) S. Yamazaki, M. Tanaka, A. Yamaguchi and S. Yamabe, J. Am. Che. Soc., 1994, 116, 2356;
23. (b) S. Yamazaki, M. Tanaka, T. Inoue, N. Morimoto, H. Kumagai and K. Yamamoto, J. Org. Chem., 1995, 60, 6546;
24. S. Yamazaki, M. Tanaka and S. Yamabe, J. Org. Chem., 1996, 61, 4046;
25. S. Yamazaki, H. Kumagai, T. Takada, S. Yamabe and K. Yamamoto, J. Org. Chem., 1997, 62, 2968;
26. (e) S. Yamazaki, T. Takada, T. Imanishi, Y. Moriguchi and S. Yamabe, J. Org. Chem., 1998, 63, 5919;
27. (f) S. Yamazaki, H. Kataoka and S. Yamabe, J. Org. Chem., 1999, 64, 2367;
28. (g) S. Yamazaki, Y. Yanase, E. Tanigawa, S. Yamabe and H. Tamura, J. Org. Chem., 1999, 64, 9521.
29. S. Yamazaki, Y. Yanase and K. Yamamoto, J. Chem. Soc., Perkin Trans. 1, 2000, 1991.