An efficient protocol for the epoxidation of acid- and acid/base-sensitive alkenes with m-chloroperoxybenzoic acid

Synthetic Communications

Volumn 26, Issue 15, 1996, Pages 2875-2880

  Svensson, Anette ^a   Lindström, Ulf M ^a   Somfai, Peter ^a  

^a LUND INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLONE DERIVATIVE; ALKENE DERIVATIVE; EPOXIDE; UNCLASSIFIED DRUG;

ARTICLE; EPOXIDATION; REACTION ANALYSIS;

EID: 0030003059     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608005222     Document Type: Article

References (8)

1. Sharpless epoxidation of 1a, using either the catalytic or stoichiometric procedure, was unsuccessful and could not be improved by using a more acid stable acetal, such as a 5,5-dimethyl-1,3-dioxane. The lability of 1,3-dioxolanes toward Sharpless epoxidations have been observed previously: Lee, A. W. M. J. Chem. Soc., Chem. Commun. 1984, 578.
2. Anderson, W. K.; Veysoglu, T. J. Org. Chem. 1973, 38, 2267.
3. Hijfte, L. V.; Little, R. D.; Petersen, J. L.; Moeller, K. D.; J. Org. Chem. 1987, 52, 4647.
4. Hanzlik, R. P.; Hubert, J. M. J. Org. Chem. 1978, 43, 610.
5. Swern, D. In Organic Peroxides; Swern, D., Ed.; Wiley: New York, 1971; Vol. 2, p 355.
6. Plesnicar, B. In Oxidation in Organic Chemistry; Trahanovsky, W. S., Ed.; Academic: New York, 1978; Vol. 5C, Chapter 3.
7. Katritzky, A. R.; Lagowski, J. M. Chemistry of the Heterocyclic N-Oxides; Academic: New York, 1971; Chapter 2.
8. For a summary of general experimental procedures see: Somfai, P. J. Chem. Soc., Perkin Trans, 1 1995, 817.