Potassium permanganate oxidation of organic compounds

It has been discovered that potassium permanganate is an effective heterogeneous oxidant, even without resorting to the use of a solid support, if acetonitrile is employed as the solvent. Primary benzylic and secondary alcohols are converted to the corresponding aldehydes and ketones, alkyl arenes, are oxidized to the corresponding a-ketones in good yields using this procedure, and both alkyl and aryl sulfides are smoothly converted to the corresponding sulfones, also in excellent yields. When methylene chloride is used as the solvent, instead of acetonitile, the yields of aldehydes, ketones, a-ketones, and sulfones are reduced. However, the oxidation of thiols to disulfides proceeds satisfactorily when methylene chloride is the solvent.