A facile two-carbon ring expansion process based on the 2-cyano-1-vinylcycloalkanol system

Tetrahedron Letters

Volumn 40, Issue 37, 1999, Pages 6753-6756

  Shia, Kak Shan ^a   Jan, Ning Wei ^a   Zhu, Jia Liang ^b   Ly, Tai Wei ^b   Liu, Hsing Jang ^a,b  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

^b UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Alcohols; Cyano compounds; Ketones; Ring transformations

Indexed keywords

ALCOHOL DERIVATIVE; CYCLOALKANOL DERIVATIVE; CYCLOALKANONE; KETONE; NITRILE; POTASSIUM DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CYCLIZATION; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0033543626     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01401-X     Document Type: Article

References (20)

1. (a) Hesse, M. Ring Enlargement in Organic Chemistry; VCH: Weinheim, 1991; pp. 53-94;
2. (b) Wilson, S. R. In Organic Reactions; Paquette, L. A.; Beak, P.; Ciganek, E.; Curran, D.; Hegedus, L.; Kelly, R. C.; Overman, L. E.; Roush, W.; Sih, C.; Smith III, A. B.; Uskokovic, M.; White, J. D., Eds.; John Wiley & Sons: New York, 1993; Vol. 43, Chapter 2;
3. Molander, G. A. Acc. Chem. Res. 1998, 31, 603-609.
4. Thies, R. W.; Daruwala, K. P. J. Org. Chem. 1987, 52, 3798-3806 and references cited therein.
5. (a) Jackson, D. K.; Narasimhan, L.; Swenton, J. S. J. Am. Chem. Soc. 1979, 101, 3989-3990;
6. (b) Cohen, T.; Ouellette, D.; Pushpananda, K.; Senaratne, A.; Yu, Lin. C. Tetrahedron Lett. 1981, 35, 3377-3380;
7. (c) Spangler, L. A.; Swenton, J. S. J. Org. Chem. 1984, 49, 1800-1806;
8. (d) Cohen, T.; Yu, L. C.; Daniewski, W. M. J. Org. Chem. 1985, 50, 4596-4600.
9. Lee, T. H.; Liao, C. C.; Liu, W. C. Tetrahedron Lett. 1996, 37, 5897-5900.
10. The structure of this compound was confirmed by X-ray analysis.
11. 19NO: 241.1467; found: 241.1465.
12. An inseparable mixture of two diastereomers (9:1) was obtained.
13. An inseparable mixture of two diastereomers (1:1) was used as the starting material.
14. Liu, H. J.; Zhu, J. L.; Shia, K. S. Tetrahedron Lett. 1998, 39, 4183-4186.
15. (a) Imamoto, T.; Takitama, N.; Nakamura, K. Tetrahedron Lett. 1985, 26, 4763-4766;
16. (b) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: New York, 1994; Section 5.4;
17. (c) Liu, H. J.; Shia, K. S.; Shang, X.; Zhu, B. Y. Tetrahedron 1999, 55, 3803-3830.
18. (a) Carpenter, B. K. Tetrahedron 1978, 34, 1877-1884;
19. (b) Wilson, S. R.; Misra, R. N.; Georgiadis, G. M. J. Org. Chem. 1980, 45, 2460-2468;
20. (c) Zoeckler, M. T.; Carpenter, B. K. J. Am. Chem. Soc. 1981, 103, 7661-7663.