Studies on Sulfenamides. II. Oxidation of 2-and 4'-Substituted Benzenesulfenanilides with Lead Dioxide

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2-and 4'-Substituted benzenesulfenanilidyl radicals were generated by the oxidations of benzenesulfenanilides (4'-OMe (1a), 4'-Me (1b), 4'-Cl (1c), 4'-H (1d)) and 2-nitrobenzene-sulfenanilides (4'-OMe (3a), 4'-Me (3b), 4'-Cl (3c), 4'-H (3d)) with lead dioxide, and their electron spin resonance (ESR) and visible spectra were investigated. The radicals generated from 1a, 1b, 3a, and 3b in benzene were fairly stable and gave well-resolved ESR spectra, whereas those from 1c, 1d, 3c, and 3d were less stable and decomposed thoroughly in an hour. The oxidations of 1a and 1b in benzene gave the corresponding 2,7-disubstituted phenazines as the final products, whereas those of 1c, 1d, 3a-d did not. The oxidations of 3a-d in acetonitrile containing 1% CF_3COOH and 1% (CF_3CO)_2O gave the corresponding phenazines and N-(2-nitrophenylthio) acetamide (6). The formation of 6 was interpreted in terms of acetamidation of the sulfenylium ion.
公益社団法人日本薬学会の論文
1979-02-25