Studies on Sulfenamides. I. Cyclic Voltammetry and Controlled Potential Electrolysis of 4'-Substituted Bezenesulfenanilides

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Anodic oxidation of benzenesulfenanilides (4'-OMe (1a), 4'-Me (1b), 4'-Cl (1c), 4'-H (1d)) were investigated by cyclic voltammetry and controlled potential electrolysis at a glassy-carbon anode in acetonitrile. The value of i_p/c of the first anodic peak, where i_p is the peak current and c is the concentration of 1a, decreased with increase in c, which was ascribed to the hydrolysis of 1a at the surface of the anode caused by the liberation of protons during the electrolysis. Electrolysis of 1a, 1b, and 1c (10 mM) gave the corresponding phenazines, whereas that of 1d did not. The nitrenes are suggested for the formation of the phenazines. Electrolysis of 1a in the presence of water (1%) gave N-phenylthio-p-quinoneimine in addition to 2, 7-dimethoxyphenazine.