Oxidation of Allylic Alcohols by Dimethyldioxirane: Competition Reaction Between Epoxidation and C-H Insertion.

Abstract Epoxidation of allylic alcohols with dimethyldioxirane is accompanied by oxidation of the hydroxy functionality; thus enone formation increases with decreasing substitution at the CC double bond; nonetheless, selective epoxidation can be obtained by acylation of the alcohol functionality.