Oxidation of unsaturated fatty acids with ruthenium and osmium tetroxide

The oxidation of the alkali metal salts of oleic and undecylenic acid with ruthenium and osmium tetroxides is reported. The oxidants are used in catalytic amounts in conjunction with an excess of the in-expensive cooxidant sodium hypochlorite. Ruthenium tetroxide cleaves the carbon-carbon double bond of potassium oleate, to give pelargonic and gives sebacic acid. With osmium tetroxide, hydroxylation of the double bond of potassium oleate gives a 95% yield oferythro-9,10-dihydroxystearic acid. The osmium tetroxide oxidation of sodium undecylenate results in the formation of 10,11-dihydroxyundecanoic acid and the cleavage product sebacic acid in varying yields.