Oxidation of hydrocarbons. 15. A study of the oxidation of alkenes by methyltributylammonium permanganate

Abstract

A study of the reduction of methyltributylammonium permanganate by a large number of alkenes in methylene chloride has dispelled a current uncertainty concerning the nature of the inorganic product obtained. It is colloidal manganese dioxide and not a manganate(V) cyclic diester as previously supposed. This product is stabilized in methylene chloride solutions by adsorption of the alkene, which decreases its polarity at the solvent interphase. The solubility of the colloid is therefore a function of both the concentration and the identity of the alkene. In certain (atypical) cases, where acidic compounds are present, the product is further reduced to manganese(III).