Retention stereochemistry of thermal 1,3-silyl migration in allylsilanes

Journal of the American Chemical Society

Volumn 121, Issue 12, 1999, Pages 2925-2926

  Zhang, Luo Cheng ^a   Kabuto, Chizuko ^b   Kira, Mitsuo ^a,b  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; CYCLOHEXANE DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; ISOMERISM; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0040758520     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983677j     Document Type: Article

References (23)

1. (a) Kwart, H.; Slutsky, J. J. Am. Chem. Soc. 1972, 94, 2515.
2. (b) Slutsky, J.; Kwart, H. J. Am. Chem. Soc. 1973, 95, 8678.
3. Takahashi, M.; Kira, M. J. Am. Chem. Soc. 1997, 119, 1948.
4. Yamabe, T.; Nakamura, K.; Shiota, Y.; Yoshizawa, K.; Kawauchi, S.; Ishikawa, M. J. Am. Chem. Soc. 1997, 119, 807.
5. In contrast, 1,3-silyl migration in β-ketosilanes has been known to proceed with retention of configuration at silicon. Brook, A. G.; MacRae, D. M.; Limburg, W. W. J. Am. Chem. Soc. 1967, 89, 5493.
6. For reviews of rearrangements of organosilicon compounds, see: (a) Brook, A. G. Acc. Chem. Res. 1974, 7, 11. (b) Brook, A. G.; Bassindale, A. R. Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: London, 1980; Vol. 2, Essay 9.
7. For reviews of rearrangements of organosilicon compounds, see: (a) Brook, A. G. Acc. Chem. Res. 1974, 7, 11. (b) Brook, A. G.; Bassindale, A. R. Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: London, 1980; Vol. 2, Essay 9.
8. 5a
9. Sakurai, H.; Murakami, M. J. Am. Chem. Soc. 1972, 94, 5080. Sakurai, H.; Murakami, M. Bull. Chem. Soc. Jpn. 1976, 49, 3185; 1977, 50, 3384.
10. Sakurai, H.; Murakami, M. J. Am. Chem. Soc. 1972, 94, 5080. Sakurai, H.; Murakami, M. Bull. Chem. Soc. Jpn. 1976, 49, 3185; 1977, 50, 3384.
11. Sakurai, H.; Murakami, M. J. Am. Chem. Soc. 1972, 94, 5080. Sakurai, H.; Murakami, M. Bull. Chem. Soc. Jpn. 1976, 49, 3185; 1977, 50, 3384.
12. Sakurai, H.; Murakami, M.; Takeuchi, K.; Kabuto, C. J. Organomet. Chem. 1988, 341, 133.
13. Hosomi, A.; Sakurai, H. Tetrahedron Lett. 1978, 29, 2589.
14. The cis and trans isomers are defined with respect to 4-tert-butyl and allylic groups.
15. Kira, M.; Taki, T.; Sakurai, H. J. Org. Chem. 1989, 54, 5647.
16. Carleer, R.; Anteunis, M. J. O. Org. Magn. Reson. 1974, 6, 617.
17. -1; 286 K. R = 0.075 (data with I > 3σ(I)), Rw = 0.074, and GOF = 6.94.
18. Altomare A.; Burla, M. C.; Camalli, M.; Cascarano G.; Giacovazzo C.; Guagliardi A. J. Appl. Crystallogr. 1994, 27, 435.
19. Details of the experimental data of all of these allylic silanes are given in the Supporting Information.
20. -1.
21. Barton, T. J.; Burns, S. A.; Davidson, I. M. T.; Ijadi-Maghsoodi, S.; Wood, I. T. J. Am. Chem. Soc. 1984, 106, 6367. See also: Walsh, R. The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.: John Wiley & Sons: New York, 1989; Part 1, Chapter 5, pp 385-386.
22. Barton, T. J.; Burns, S. A.; Davidson, I. M. T.; Ijadi-Maghsoodi, S.; Wood, I. T. J. Am. Chem. Soc. 1984, 106, 6367. See also: Walsh, R. The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.: John Wiley & Sons: New York, 1989; Part 1, Chapter 5, pp 385-386.
23. J. Am. Chem. Soc. 1999, 121, 2927-2928