Radical reactions of epoxides. Chlorine-atom abstraction from. alpha.-and. beta.-chloro epoxides by the triphenyltin radical

KW Krosley, GJ Gleicher, GE Clapp

Index: Krosley, Kevin W.; Gleicher, Gerald Jay; Clapp Gary E. Journal of Organic Chemistry, 1992 , vol. 57, # 3 p. 840 - 844

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Citation Number: 27

Abstract

The four isomers of chloroepoxypropane have been prepared, and their relative reactivities with triphenyltin hydride have been determined. The three a-chloroepoxypropanes react at a much slower rate than does epichlorohydrin, the only Fchloro epoxide of the four. The nature of the increased reactivity for the f?-chloro epoxidea has been investigated by studying two pair of diastereomeric@-chloro epoxides, and a single acyclic f?-chloro ether. The results ...