Replacement of Hydrogen at a Tertiary Carbon Atom with OH by Alkaline Permanganate1

RH Eastman, RA Quinn

Index: Eastman,R.H.; Quinn,R.A. Journal of the American Chemical Society, 1960 , vol. 82, p. 4249 - 4252

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Citation Number: 16

Abstract

The use of an alkaline solution of potassium permanganate as an oxidizing agent in organic chemistry is ordinarily reserved for attack on double bonds, easily oxidized functions such as alcohols and aldehydes, and saturated centers which are activated by an attached aromatic ring. We were accordingly surprised at the slow but relatively smooth conversions of the isomeric sabinene hydrates (Ia, b) into the diols IIa, b by the reagent. 2 Although instances ...