Reaction of Benzeneseleninyl Chloride with Olefins in the Presence of a Lewis Acid. A Novel One Step Vinylic Chlorination

Abstract In the presence of aluminum chloride benzeneseleninyl chloride was found to be an excellent vinylic chlorinating reagent of olefins under mild conditions. However, such olefins as styrene, trans-stilbene, and trans-1-phenylpropene afforded dichloro adducts under similar conditions. A plausible reaction mechanism involving positive chlorine intermediate is proposed.