Reactivity of vinyl sulphonic esters. Part III. Reactivity of arylthiovinyl sulphonates with nucleophiles

Abstract

1,2-Diaryl-2-arylthiovinyl 2,4,6-trinitrobenzenesulphonates react with weak nucleophiles (methanol, hydrogen chloride, or arenethiols) in dichloromethane to give products of substitution of the sulphonic residue by the nucleophiles. Reactions with strong nucleophiles (benzenethiolate ion or piperidine) are different, indicative of an interaction of the nucleophiles with the activated aromatic ring of the arenesulphonic residue. The results are discussed in terms of a mechanism of unimolecular substitution at an ethylenic carbon.