Unsymmetrical Target Disulfides from Transient Sulfenic Acids

Abstract

In accordance with our research interests devoted to the development of synthetic procedures involving sulfenic acids as intermediates, their condensation with various thiols has been exploited as an easy and versatile methodology to obtain unsymmetrical disulfides. Even if this reaction is well known, to the best of our knowledge it has never been used before as a methodology to synthesize unsymmetrical disulfides. The mild generation of mono-, di-, and tri-sulfenic acids from different sulfoxide precursors, depending on the required reaction conditions, allows the presence of even base/acid-sensitive and thermolabile functional groups and the synthesis, in excellent yields, of various kinds of unsymmetrical disulfides, some of which carry typical moieties of natural substances.

Keywords:

• Condensation
• disulfides
• sulfenic acids
• thiols

Acknowledgments

This work was supported by the Ministero dell’Istruzione, dell’Università e della Ricerca, and the Università degli Studi di Messina, Italy (PRIN 2008).