Oxidative Cleavage of Alkenes

In basic conditions, treatment of alkene with potassium permanganate forms a vicinal diol. Oxidative cleavage by permanganate in neutral or acidic conditions, however, leads to cleavage to form carbonyl compounds by means of the same cyclic manganate ester intermediate. Where ozonolysis, another method of oxidative cleavage of alkenes, produces an aldehyde or formaldehyde, cleavage with permanganate produces a carboxylic acid or carbon dioxide respectively.