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N-Unsubstituted sulfilimines, when reacted with sodium hypochlorite in an aqueous alkaline methanol solution or with Chloramine-T in dry acetonitrile in the presence of excess sodium salt of tosylamide were converted to the corresponding N-unsubstituted sulfoximines (1) or mono-N-tosylsulfonediimines (2) in good yields. 2 gave the unsubstituted sulfonediimines (3) in high yields upon treatment with conc. H2SO4. N-Chlorosulfilimine (5) was isolated in the initial stage of these reactions. 5 was found to react with NaOH in aqueous methanol and also with anhydrous Chloramine-T in dry acetonitrile to yield the corresponding 1 and 2 in good yields. IR, NMR, and Mass spectroscopic studies of 1, 2, and 3 were also carried out.
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Furukawa et al. (1984) studied this question.
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