Synthesis and Characterization of (Methoxy(thiocarbony1))sulfenyl Chloride

Alayne L. Schroll, Steven J. Eastep, George Barany

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(Methoxy(thiocarbony1))sulfenyl chloride (1), a previously elusive compound, has now been generated by cleavage of methoxy(thiocarbonyl) N-methyl-N-phenylamino sulfide (7) with gaseous hydrogen chloride. The sulfenyl chloride 1 had limited stability and was characterized by trapping with O, O'-dimethyl thiocarbonate or with methanethiol to yield (methoxycarbonyl)(methoxy(thiocarbony1))disulfane (8) or (methoxy(thiocarbonyl))-methyldisulfane (9), respectively. Chlorination of acetyl methoxy(thiocarbonyl) sulfide (6) could be arrested at 1 plus acetyl chloride, and further chlorination of 1 provided (methoxydichloromethyl)disulfanyl chloride (5).

Original languageEnglish (US)
Pages (from-to)1475-1479
Number of pages5
JournalJournal of Organic Chemistry
Issue number5
StatePublished - Jan 1 1990


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