Reactions of halogenated acrylonitrile derivatives with arylsulfinate salts: A novel chain shortening reaction

Abstract

Reaction of α,β-dichloroacrylonitrile with arylsulfinate salts in refluxing ethanol gave high yields of arylsulfonylacetonitriles. A proposed intermediate, α-chloro-β- p-tolylsulfonylacrylonitrile can be isolated and can be converted to p-tolylsulfonylacetonitrile under the conditions of the reaction. β,β-Dichloroacrylonitrile similarly gives acetonitrile derivatives on reaction with sulfinate salts.