Photolysis and thermolysis of N-(N-arylimidoyl)sulphimides

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Abstract
Routes to the imidoylsulphimides (1) are described, starting from either the corresponding amidines or the imidoyl chlorides. Photolysis of the sulphimides involves cleavage of the sulphur–nitrogen bonds and gives 2-substituted benzimidazoles in good yields. SS-Dimethyl-N-(N-phenylbenzimidoyl)sulphimide (1a) is decomposed by heating in benzonitrile or decalin under reflux, and gives 2-phenylbenzimidazole, 2-phenylquinazoline, and 2,4,6-triphenyl-1,3,5-triazine. Mechanisms are proposed for the formation of the last two, unexpected products. Similar thermal decomposition of the sulphimides (1b–e) is observed; the thermolysis is markedly catalysed by copper salts.

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