Radical Reactions of Epoxides. Chlorine Atom Abstraction from α- and β-Chloro Epoxides by the Triphenyltin Radical

Article abstract of DOI:10.1021/jo00029a011

The four isomers of chloroepoxypropane have been prepared, and their relative reactivities with triphenyltin haydride have been determined.The three α-chloroepoxypropanes react at a much slower rate than does epichlorohydrin, the only β-chloro epoxide of the four.The nature of the increased reactivity for the β-chloro epoxides has been investigated by studying two pair of diastereomeric β-chloro epoxides, and a single acyclic β-chloro ether.The results are discussed in terms of the inductive, and stereoelectronic effects of the epoxide.