The reactions of mercaptide anions with chlorinated sulfones

Abstract

Mercaptide anions react with chlorinated sulfones in two modes, i.e. nucleophilic attack on carbon with chlorine as the leaving group and/or nucleophilic attack on chlorine with concomitant carbanion formation. Mercaptide anion pKb, degree of chlorination of the sulfone substrate, and substituent effects are qualitatively assessed in terms of the propensity for nucleophilic attack at carbon or chlorine.