Numerous methods have been developed for the oxidation of sulfides1p2 to sulfoxides in reactions usually giving the sulfoxide contaminated with sulfide and/or sulfone. More recently the use of t-butyl hypochlorite as a reagent for the oxidation of sulfides to sulfoxides has been r e p~r t e d .~,~ These reports prompted us to disclose our results on the use of N-halosuccinimides in methanol as the oxidizing agents. It has been previously shown5 that aromatic sulfides are oxidized cleanly to sulfoxides in aqueous media when treated with I\;-bromosuccinimide, but that aliphatic sulfides undergo C-S bond cleavage under identical conditions. I n our study, the oxidation of sulfides was carried out in anhydrous methanol employing N-bromo- (SBS) and N-chlorosuccinimide (KCS). Sulfoxides were iso-(7) P. S. NOTES 3977were characterized by their ir spectra, refractive indices, and elemental analyses.The solid sulfoxides were isolated by dissolving the mixture in 200 ml of methylene chloride and washing thoroughly with water. After the solution was dried and the solvent was evaporated, the solids were recrystallized.

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