Hydroxy sulfoxides derived from norbornene: determination of stereochemistry, and synthesis by stereoselective oxidation

Abstract

The structure (5) of one of the hydroxy sulfoxides formed by thiol-oxygen cooxidation of norbornene has been determined by X-ray diffraction. Other products have been related to it by appropriate chemical transformations. The stereospecific, or highly stereoselective, conversion of suitable hydroxy sulfides into one of the two possible diastereoisomeric hydroxy sulfoxides demonstrates the directive influence of the hydroxyl group on oxidation of vicinal sulfur.