Effect of β-substituents on the regioselectivity of the diazomethane ring expansion of α-methyl-α-methoxycyclobutanones to cyclopentanones

Journal of Organic Chemistry

Volumn 64, Issue 9, 1999, Pages 3306-3311

  Reeder, Lisa M ^a   Hegedus, Louis S ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTANONE DERIVATIVE; CYCLOPENTANONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033617452     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990226o     Document Type: Article

References (20)

1. For reviews, see: (a) Bellus, D.; Ernst, B. Angew. Chem., Int. Ed. Engl. 1987, 27, 797. (b) Lee-Ruff, E. New Synthetic Pathways from Cyclobutanones. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press: Greenwich, CT, 1991; Vol. 1.
2. For reviews, see: (a) Bellus, D.; Ernst, B. Angew. Chem., Int. Ed. Engl. 1987, 27, 797. (b) Lee-Ruff, E. New Synthetic Pathways from Cyclobutanones. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press: Greenwich, CT, 1991; Vol. 1.
3. Tidwell, T. T. Ketenes; John Wiley and Sons: New York, 1995; and references therein.
4. For a review, see: Hegedus, L. S. Tetrahedron 1997, 53, 4105.
5. Brown, B.; Hegedus, L. S. J. Org. Chem. 1998, 63, 8012.
6. Miller, M. W.; Hegedus, L. S. J. Org. Chem. 1993, 58, 6779.
7. Kedar, T. E.; Miller, M. W.; Hegedus, L. S. J. Org. Chem. 1996, 61, 6121.
8. Reed, A. D.; Hegedus, L. S. Organometallics 1997, 16, 2313.
9. For reviews, see: (a) Wovkulich, P. M. Skeletal Reorganizations: Chain Extension and Ring Expansion. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, U.K., 1991; Vol. 1, pp 843-861. (b) Reference 9.
10. For reviews, see: (a) Wovkulich, P. M. Skeletal Reorganizations: Chain Extension and Ring Expansion. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, U.K., 1991; Vol. 1, pp 843-861. (b) Reference 9.
11. Wong, H. C. N. Houben-Weyl Methods of Organic Chemistry; de Meijere, A., Ed.; Georg Thieme Verlag: Stuttgart, Germany, 1997; Vol. E17e, pp 495-515.
12. Diazomethane was prepared from Diazald according to Aldrich Technical Information Bulletin No. AL-180.
13. (a) de Azevedo, M. B. M.; Greene, A. E. J. Org. Chem. 1995, 60, 4940.
14. (b) Nebois, P.; Greene, A. E. J. Org. Chem. 1996, 61, 5210.
15. Bao, J.; Wulff, W. D.; Dominy, J. B.; Fumo, M. J.; Grant, E. B.; Rob, A. C.; Whitcomb, M. C.; Yeung, S.-M.; Ostrander, R. L.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 3392.
16. Soderberg, B. C.; Hegedus, L. S.; Sierra, M. A. J. Am. Chem. Soc. 1990, 112, 4364.
17. Quallich, G. J.; Lackey, J. W. Tetrahedron Lett. 1990, 31, 3685.
18. For the synthesis of 3-vinyl-(S)-4-phenyl-2-oxazolidinone, see ref 5.
19. For the synthesis of vinyl ethers, see: Watanabe, W. H.; Conlon, L. E. J. Am. Chem. Soc. 1957, 79, 2828.
20. Mr. Brian Brown is gratefully acknowledged for providing samples of 5a and 5b.