PERIODATE–PERMANGANATE OXIDATIONS: I. OXIDATION OF OLEFINS

Abstract

It was discovered that olefinic double bonds are readily oxidized in an aqueous solution of periodate which contains only catalytic amounts of permanganate. The data suggest that in the effective pH range of 7 to 10 the permanganate is not reduced at once beyond the manganate state and that it is regenerated from this state by periodate action. Evidence was obtained that the main course of the oxidation of an olefin of type —CH=CH— involves first permanganate oxidation to hydroxyketones which are then rapidly cleaved by periodate to products which may subsequently be oxidized by the permanganate.