α,β-Epoxy Sulfoxides as Useful Intermediates in Organic Synthesis. IX. A Novel Synthesis of Alkyl Vinyl Ketones and Divinyl Ketones from Carbonyl Compounds and 1-Chloro-3-phenylthiopropyl Phenyl Sulfoxide as a Three-Carbon Homologating Agent

Article abstract of DOI:10.1246/bcsj.60.301

The α,β-epoxy sulfoxides easily derived from carbonyl compounds and 1-chloro-3-phenylthiopropyl phenyl sulfoxide were treated with sodium benzeneselenolate to give β-phenylthio carbonyl compounds in excellent yields.The phenylthio group was oxidized to the sulfinyl group and was then treated with a base to afford alkyl vinyl ketones in quite good yields.This reaction presents a novel method for the preparation of alkyl vinyl ketones from carbonyl compounds by three-carbon homologation.The treatment of α,β-epoxy sulfoxides mentioned above with benzenethiolate gave α,β'-bis(phenylthio) ketones.The elimination of the both thio groups afforded divinyl ketones.