Oxidation of Alkenes to Vicinal Diols

Both of the above oxidation mechanisms proceed by syn addition. To accomplish anti hydroxylation of alkenes, the method to employ is hydrolysis of epoxides. As shown above, in basic conditions, oxidation of alkene with potassium permanganate results in formation of vicinal diol, but with acidic or neutral conditions, complete cleavage occurs to produce carboxylic acids or ketones (or carbon dioxide).