Homogeneous Permanganate Oxidation in Non-Aqueous Organic Solution. Selective Oxidations of Olefins Into 1,2-Diols or Aldehydes

Potassium permanganate solubilized in dichloromethane by use of equimolar amount of triethylbenzylammonium chloride smoothly oxidized olefins to give homogeneous dark brown reaction mixtures, which were then selectively decomposed into either 1,2-diols or aldehydes in good yields by treatment with aqueous solutions depending upon pH.