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Oxidation of 3‐amino‐4‐(4‐chlorophenyl)furazan (1) and its phosphine imine derivative, 3‐(4‐chlorophenyl)‐4‐trioctylphosphiniminofurazan (3), with dimethyldioxirane (DMD) gave 3‐(4‐chlorophenyl)‐4‐nitrofurazan (4) as the exclusive product. However, the sulfilimine derivative, 3‐(4‐chlorophenyl)‐4‐dimethylsulfiliminofurazan (2), was converted by DMD to the sulfoximine, 3‐(4‐chlorophenyl)‐4‐dimethylsulfoximinofurazan (6). These results contrast dramatically with the oxidations of these compounds with peracids.
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Michael D. Coburn (1989) studied this question.
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