Transformations of penicillins. Part VII. Vinylic sulphoxides from penicillins and their reactions

Abstract

The sulphenic acid intermediates produced thermally from penicillin S-oxides undergo addition to acetylenic esters to produce conjugated sulphoxides in good yields. These vinylic sulphoxides are subject to nucleophilic addition reactions, with, for example, diethyl sodiomalonate, which proceed in a stereoselective manner. Intramolecular addition reactions have also been observed.