Journal of the Chemical Society. Perkin transactions I p. 1039 - 1044 (1985)
Update date:2022-08-03
Topics:
Bewick, Alan
Mellor, John M.
Owton, W. Martin
Reactions of alkenes with di-n-propyl, diphenyl, and dibenzyl disulphide in the presence of lead(IV) salts in trifluoroacetic acid-dichloromethane are described.The products, vicinal trifluoroacetoxysulphides, are obtained in higher yields with manganese(III) salts as the oxidant.Alternative reaction conditions with use of iron(III) salts or in the absence of added metal salts are also described.Trifluoroacetoxysulphides derived from diphenyl disulphide react with acetonitrile under Ritter conditions to give acetamidosulphides but trifluoroacetoxysulphides derived from dibenzyl disulphide only give the vicinal acetamidosulphides in poor yield as a result of an alternative reaction pathway affording benzylacetamide.Conversions of acetamidosulphides into aminosulphides and into acetamidothiols are described.
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