The Cathodic Desulfonylation of 1-Ethoxycarbonyl- and 1-Cyano-1-(p-tolylsulfonyl)-2-phenylethenes at the Mercury Electrode in Nonaqueous Solvents

Article abstract of DOI:10.1246/bcsj.61.3329

The cathodic reduction of 1-ethoxycarbonyl-1-(p-tolylsulfonyl)-2-phenylethene in MeCN and DMF is characterized by the selective elimination of the p-tolylsulfonyl group, resulting in the formation of ethyl (E)-cinnamate in good yields, in the presence of such efficient proton donors as benzoic acid and acetic acid.On the other hand, the cathodic desulfonylation of 1-cyano-1-(p-tolylsulfonyl)-2-phenylethene proceeds with low efficiencies, even in the presence of acetic acid and benzoic acid.