Issue 11, 1991

Electrochemical reduction of substituted isothiazole-3-thiones in aprotic media

Abstract

The title compounds are obtained in good yields from 1,2-dithiole-3-thiones. Using cyclic voltammetry in dimethylformamide, two kinds of behaviour are evidenced and discussed in terms of the aromaticity of the 5-substituent (Ar). With Ar = pyrazinyl or pyridazinyl, isothiazole-3-thiones undergo an electrochemical chemical electrochemical mechanism and the rate constant of the chemical step has been deduced from voltammetric measurements. When the aromaticity increases (Ar = pyridyl or phenyl) an apparent one-step irreversible two-electron addition occurs. Whatever the nature of Ar the resulting two-electron reduction product has been isolated after controlled-potential electrolysis (CPE). In addition, in acetonitrile, CPE affords a thiophene derivative as a secondary product.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1991, 1763-1768

Electrochemical reduction of substituted isothiazole-3-thiones in aprotic media

T. Martens and M. Fleury, J. Chem. Soc., Perkin Trans. 2, 1991, 1763 DOI: 10.1039/P29910001763

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