Preparation of Functionalized Unsymmetrical Disulfides by a Base-induced Crossed Reaction of Symmetrical Disulfides

Abstract

Highly functionalized, unsymmetrical disulfides (presumed metabolites of a bioactive sulfide) were synthesized by a base-induced, crossed reaction of two different symmetrical disulfides. The reaction was also applied to the preparation of a vitamin B1 derivative, Prosultiamine.

The synthesis of thiols, selenols, sulfides, selenides, sulfoxides, selenoxides, sulfones and selenones

“…15 Unsymmetrical disulfides bearing extensive functionality have been prepared by a base-induced cross-reaction with symmetrical disulfides (Scheme 8). 16 Finally, cyclic disulfides have been prepared in good yield from bisthiocyanates by treatment with fluoride sources (Scheme 9). 17 The preparation of fluorous diaryl diselenides has recently been described.…”