Electrophilic addition of benzeneselenenyl chloride to alkenes bearing an electron-withdrawing substituent

Abstract

Reaction of benzeneselenenyl chloride with alkenes bearing electron-withdrawing substituents was found to afford a mixture of regioisomeric adducts formed via the electrophilic addition of the phenylseleno group. The isomer distribution can be accounted for by postulating the interaction in the episelenonium ion intermediate of the phenylseleno group with the electron-withdrawing substituent.