Oxidation of organic sulfides by N-halamine compounds

Akdag A., Liang J., Worley S. D.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, vol.182, no.7, pp.1525-1533, 2007 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 182 Issue: 7
  • Publication Date: 2007
  • Doi Number: 10.1080/10426500701247102
  • Journal Name: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1525-1533
  • Keywords: N-halamines, organic sulfides, oxidation, polymer bound reagents, 2-CHLOROETHYL ETHYL SULFIDE, DIMETHYL-SULFOXIDE, SULFUR MUSTARD, SILICA-GEL, BROMOSUCCINIMIDE, DERIVATIVES, MOLECULES, MECHANISM, POLYMERS, BEADS
  • Middle East Technical University Affiliated: Yes

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.