Sulfenylation of Active Methylene Compounds with Sulfenamides

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Abstract
Equimolar reactions of sulfenamides derived from secondary alkylamines with active methylene compounds afforded mono-sulfenylated compounds in good yields. The reactions of 2 mol of sulfenamides derived from imides with 1 mol of active methylene compounds in the presence of a base gave di-sulfenylated compounds. It was found that α-mono-sulfenylated ketones were prepared by the reactions of enamines with sulfenamides derived from imides. α-gem-Di-sulfenylated ketones were prepared by the reactions of α-mono-sulfenylated ketones with sulfenamides derived from imides in the presence of a base. The preparation and reactions of N-phenylthiobenzamidine hydrochloride were also examined.