The cathodic desulfonylation of 1-ethoxycarbonyl- and 1-cyano-1-(p-tolylsulfonyl)-2-phenylethenes at the mercury electrode in nonaqueous solvents.
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概要
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The cathodic reduction of 1-ethoxycarbonyl-1-(<I>p</I>-tolylsulfonyl)-2-phenylethene in MeCN and DMF is characterized by the selective elimination of the <I>p</I>-tolylsulfonyl group, resulting in the formation of ethyl (<I>E</I>)-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-(<I>p</I>-tolylsulfonyl)-2-phenylethene proceeds with low efficiencies, even in the presence of acetic acid and benzoic acid.
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