Oxidative Functionalization of the β-Carbon in α,β-Unsaturated Systems. Preparation of 3-Phenylthio Enones, Acrylates, and Other Vinyl Derivatives

Article abstract of DOI:10.1021/jo00315a002

The β-carbon of α,β-unsaturated ketones, esters, lactones, and nitriles can be oxidatively functionalized in a regiospecific manner in a simple sequence of reactions.Michael addition of thiophenol followed by oxidation with N-chlorosuccinimide gives chloro sulfides that readily lose HCl to give 3-phenylthio enones, acrylates, and other vinyl derivatives.