Oxidation of Organic Sulfides by N-Halamine Compounds

Abstract

N-halamine chemistry has been an important research topic in these laboratories for over two decades, offering many exciting opportunities both from practical and pedagogical points of view. One of these opportunities is in the use of polymer- and silica gel-bound N-halamines as selective oxidizing agents for organosulfur compounds. In this study, they have been employed to selectively oxidize organic sulfides including dimethyl sulfide and chloroethyl ethyl sulfide, the chemical mustard stimulant. The latter oxidation produced the less toxic sulfoxide derivative with about 70% conversion, with no sulfone produced, and only about 30% accompanying conversion to sulfoxide hydrolysis products. In this article, we report a combination of experimental and computational results.

Keywords:

• N-halamines
• organic sulfides
• oxidation
• polymer bound reagents

Acknowledgments

This work has been supported by The US Air Force through Contract F08637-02-C-7020 and the HaloSource Company. The authors thank Drs. J. F. Williams and M. L. Mckee for helpful discussions during the course of this work. The computer time was provided by the Alabama Supercomputer facility.