Benzenesulfenanilidyl radicals (3) were generated by the oxidation of benzenesulfenanilides (4'-OMe (1a), 4'-Me (1b), 4'-Cl (1c), 4'-H (1d)) with lead dioxide, and their electron spin resonance (ESR) and visible spectra were investigated. The radicals generated from 1a and 1b in benzene were fairly stable and gave well-resolved ESR spectra, whereas those from 1c and 1d were less stable and gave poorly resolved ESR spectra. The oxidations of 1a and 1b gave the corresponding phenazines as the final products, whereas those of 1c and 1d did not.
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Sayo et al. (1977) studied this question.