Oxidation of Methyl (Methylthio)methyl Sulfoxide

Article abstract of DOI:10.1246/bcsj.53.1414

Oxidation of methyl (methylthio)methyl sulfoxide (2) with hydrogen peroxide in acetic acid or methanol produced bis(methylsulfinyl)methane in high yield.Similar results were obtained in oxidation of 2 with ozone, sodium metaperiodate, and m-chloroperbenzoic acid.In contrast, methyl (methylthio)methyl sulfone (4) was exclusively formed when oxidation of 2 with hydrogen peroxide was carried out in methanol in the presence of sodium hydroxide.Furthermore, we established a convenient and efficient method of preparing 4 by oxidation of 2 with potassium permanganate.