A novel method for the preparation of unsymmetrical bis (di- and trisulfides) via trityl sulfenyl chlorides: Precursors for cyclic polysulfides

Abstract

When triphenylmethanesulfenyl chloride 6 [(C₆H₅)₃CSCl] and its thio homologue 7 [(C₆H₅)₃CSSCl] were treated with dithiols, unsymmetrical bis(di- and trisulfides) 11 and 12 were produced in high yields. Final products were determined by ¹H and ¹³C NMR as well as by elemental analysis. The X-ray crystallographic structures of p-di(methylenedithiotrityl)benzene 11a and p-di(methylenetrithiotrityl)benzene 12a were obtained. In addition, cyclic polysulfide 13 was produced in high isolated yield via 11c.

Keywords:

• Methylenedithiotrityl
• Methylenetrithiotrityl
• Dimethanethiol
• Methanesulfenyl chloride
• Methanethiosulfenyl chloride
• Cyclic polysulfides
• Disulfides
• Trisulfides

Acknowledgements

We thank the Natural Sciences and Engineering Research Council (NSERC) of Canada and the American University of Sharjah (AUS) for financial support of this work.