Reactions of bromotrifluoromethane and related halides. Part 12. Transformation of disulfides into perfluoroalkyl sulfides in the presence of sulfoxylate anion radical precursors

Abstract

Perfluoroalkyl sulfides are prepared by reaction of perfluoroalkyl halides with disulfides in the presence of sulfoxylate anion radical precursors. Aliphatic, aromatic and heteroaromatic disulfides bearing cyano, ester and amino functional groups have been employed; a variety of perhalogenoalkanes can also be employed, e.g. CF₃(CF₂)_nI, CF₃Br, CF₂Br₂, CF₂BrCl, CFCl₃ and CF₂ClCFCl₂. The most convenient sulfoxylate anion radical precursor for this reaction is formed by a combination of sodium formate and sulfur dioxide.