Radical reactions of epoxides. Chlorine-atom abstraction from .alpha.- and .beta.-chloro epoxides by the triphenyltin radical
作者:Kevin W. Krosley、Gerald Jay Gleicher、Gary E. Clapp
DOI:10.1021/jo00029a011
日期:1992.1
The four isomers of chloroepoxypropane have been prepared, and their relative reactivities with triphenyltin hydride have been determined. The three alpha-chloroepoxypropanes react at a much slower rate than does epichlorohydrin, the only beta-chloro epoxide of the four. The nature of the increased reactivity for the beta-chloro epoxides has been investigated by studying two pair of diastereomeric beta-chloro epoxides, and a single acyclic beta-chloro ether. The results are discussed in terms of the inductive, resonance, and stereoelectronic effects of the epoxide.
Tomashevskii, A. A.; Sokolov, V. V.; Potekhin, A. A., Russian Journal of Organic Chemistry, 1994, vol. 30, # 10, p. 1610 - 1618
作者:Tomashevskii, A. A.、Sokolov, V. V.、Potekhin, A. A.