α??Imino sulfenates and α??imino sulfoxides via electrophilic alkylation of amino sulfines (thioamide S??oxides)

BG Lenz, B Zwanenburg

Index: Lenz, Bodo G.; Zwanenburg, Binne Recueil: Journal of the Royal Netherlands Chemical Society, 1984 , vol. 103, # 12 p. 342 - 347

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Abstract

Abstract Treatment of amino sulfines (thioamide S-oxides) 1 with triethyloxonium tetrafluoroborate, followed by sodium carbonate, leads to α-imino sulfenates 3. Reaction of 3 with primary and secondary amines gives α-imino sulfenamides 5. Treatment of amino sulfines with sodium hydride, followed by an alkyl halide, leads to the formation of α-imino sulfoxides 6, which are extremely sensitive towards hydrolysis. With ketenes, the imines 6 ...