1,5-Hydride shift in the aluminum chloride promoted allylsilylation of 5-silyl-1-alkenes

Organometallics

Volumn 17, Issue 12, 1998, Pages 2409-2413

  Choi, Geun Mook ^a   Yoo, Bok Ryul ^a   Lee, Ho Jin ^a   Lee, Kang Bong ^a   Jung, Il Nam ^a  

^a Korea Institute of Science and Technology   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013649770     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9710475     Document Type: Article

References (25)

1. Yeon, S. H.; Lee, B. W.; Yoo, B. R.; Suk, M. Y.; Jung, I. N. Organometallics 1995, 14, 2361.
2. Cho, B. K.; Choi, G. M.; Jin, J.-I.; Yoo, B. R.; Jung, I. N. Organometallics 1997, 16, 3576.
3. Choi, G. M.; Yeon, S. H.; Jin, J.-I.; Yoo, B. R.; Jung, I. N. Organometallics 1997, 16, 5158.
4. Yeon, S. H.; Han, J. S.; Hong, E.; Do, Y.; Jung, I. N. J. Organomet. Chem. 1995, 499, 159.
5. (a) Asao, N.; Yoshikawa, E.; Yamamoto, Y. J. Org. Chem. 1996, 61, 4974.
6. (b) Yoshikawa, E.; Gevorgyan, V.; Asao, N.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 6781.
7. Colvin, E. W. Silicon in Organic Synthesis', Butterworth: London, 1981.
8. Weber, W. P. Silicon Reagents for Organic Synthesis; Springer: Berlin, 1983.
9. Fleming, I.; Dunoguès, J.; Smithers, R. Organic Reactions; Wiley: New York, 1989; Vol. 37.
10. Hosomi, A.; Sakurai, H. Tetrahedron Lett. 1976, 17, 1295.
11. Seyferth, D.; Pornet, J.; Weinstein, R. M. Organometallics 1982, 1, 1651.
12. Hosomi, A.; Sakurai, H. J. Am. Chem. Soc. 1977, 99, 1675.
13. Fleming, I.; Paterson I. Synthesis 1979, 446.
14. 1H NMR Spectra, 1st ed.; Aldrich Chem. Co., Inc.: Milwaukee, WI, 1993; Vol. 1, pp 77-78.
15. An isomerization reaction of 1d (220 mg. 1.21 mmol) to 6e was tested in the presence of anhydrous aluminum chloride (16 mg, 0.12 mmol) and chlorotrimethylsilane (66 mg, 0.60 mmol) and with decane (100 mg) as an internal standard. The progress of the reaction was monitored by GLC.
16. One of the reviewers suggested an alternative mechanism involving a dehydrosilylation and a rehydrosilylation reactions for the isomerization of 1d to 5e. This mechanism was ruled out because the expected products, 1-allyl-1-cycloalkene and 3-(trimethylsilyl)propyl-1-cycloalkene, were not observed.
17. Olah, G. A.; Bach, T.; Prakash, G. K. S. J. Org. Chem. 1989, 54, 3370.
18. Olah, G. A.; Bach, T.; Prakash, G. K. S. New J. Chem. 1991, 15, 571.
19. Jenkins, P. R.; Gut, R.; Wetter, H.; Eschenmoser, A. Helv. Chim. Acta 1979, 62, 1922.
20. Kira, M.; Hino, T.; Sakurai, H. Tetrahedron Lett. 1989, 30, 1099.
21. Atkinson, R. S.; Green, R. H. J. Chem. Soc., Perkin Trans. 1 1974, 394.
22. Kirchen, R. P.; Okazawa, N.; Ranganayakulu, K.; Rauk, A.; Sorensen, T. S. J. Am. Chem. Soc. 1981, 103, 597.
23. (a) Sato, T.; Hayashi, M.; Hayata, T. Tetrahedron 1992, 48, 4099.
24. (b) Yoshimatsu, M.; Hatae, N.; Shimizu, H.; Kataoka, T. Chem. Lett. 1993, 1491.
25. Seyferth, D.; Jula, T. F. J. Organomet. Chem. 1968, 11, 63.