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.
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