The Journal of Organic Chemistry

Electrochemical Reduction of Pyridine-and Benzene-Substituted n-Alkyl Esters and Thioic S-Esters in Acetonitrile

RD Webster, AM Bond

Index: Webster, Richard D.; Bond, Alan M. Journal of Organic Chemistry, 1997 , vol. 62, # 6 p. 1779 - 1787

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Citation Number: 23

Abstract

Bulk controlled potential electrolysis experiments have been performed on a wide range of n- alkyl-substituted esters and thioic S-esters of pyridine and benzene in dry acetonitrile with tetraalkylammonium salts as the supporting electrolyte. In most cases, the bulk one-electron reduction of oxygen esters results in unstable or semistable radicals being formed that decompose via loss of the alkyl radical to leave the carboxylate anion in high yield (ca. 70- ...