A Versatile One‐Pot Synthesis of Dialkyl Disulfides and Sulfides

Abstract

Conversions of monofluoroalkyl and alkyl bromides to the corresponding dialkyl disulfides in a one‐pot synthesis using thiourea followed by basic hydrogen peroxide are described. Modified methods afford access to unsymmetrical disulfides and sulfides.

Keywords:

• Disulfides
• fluorine and fluorine compounds
• sulfides

Acknowledgments

We thank Dr. Allen L. Johnson for helpful discussions, Mahin Behnia for technical assistance and Milagro Navarro for some preparations and GC analyses. The Nevada NSF EPSCoR Program provided for the purchase of a ¹⁹F (5 mm) probe and material support.

Notes

¹This paper was apparently not abstracted by Chemical Abstracts. It is a convincingly documented example of the synthesis of a volatile alkanethiol via the ITUS route.

²Solvation of peroxyanions ROO⁻ inhibits reactions with sulfoxides. We found that HOO⁻ evidently reacts with the thiolate ion in preference to DMSO.