A simple method for the preparation of N-sulfonylsulfilimines from sulfides

While excellent methods exist for the oxidation of sulfides to sulfoxides (RRS)-R-1-S-2 --> (RRSO)-R-1-S-2, the aza-version of this atom transfer redox process, i.e., (RRS)-R-1-S-2 --> (RRS)-R-1-S-2=N-(SOR3)-R-2, has been less reliable. In sulfilimine synthesis, sulfoxide has been an inevitable byproduct in all cases to date, and the yields of sulfilimine have varied widely. A nearly ideal procedure for the sulfide to sulfonyl sulfilimine transformation is described. Almost quantitative yields are achieved from a diverse set of sulfides and a broad range of the readily available sulfonyl nitrenoid sources known as chloramine salts ((RSO2NClNa)-S-3), essentially by simply stirring them together in acetonitrile.