Abstract
AbstractThe reactions of ruthenium VIII tetroxide (RuO4) and the ruthenium VII and VI oxyanions, perruthenate (RuO4−) and ruthenate (RuO4=) with hydroxy substituted and unsaturated fatty acids have been studied. At a 1:1 molar ratio, ruthenium tetroxide (RuO4) and both oxyanions (RuO4− and RuO4=) oxidized 12‐hydroxystearic acid to 12‐ketostearic acid. With 9, 10‐dihydroxystearic acid, the type of oxidation products obtained depended on the amount of ruthenium oxidant used. At high ratios of oxidant to substrate, cleavage to pelargonic and azelaic acids occurred whereas at lower ratios, partial oxidation to diketo and acyloin derivatives predominated. The oxidation of oleic acid with excess ruthenium tetroxide (RuO4) or perruthenate anion (RuO4−) gave the cleavage products pelargonic and azelaic acid through the intermediate formation of dihydroxy and diketo intermediates. Ruthenate anion (RuO4=) did not react with the double bond of oleic acid.
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