Intramolecular homolytic displacement of bromine atoms from carbon in the reaction of but-3-enyl bromides with radicals

Abstract

The homolytic displacement of bromine atoms from 1-bromo-1-cyano-2,2-dimethylbut-3-ene by trichloromethyl radicals takes place by a stepwise mechanism in which a trichloromethyl radical attacks carbon-4 to give an intermediate radical which can undergo an intramolecular cyclisation with loss of a bromine atom or a radical transfer reaction with the addend.