Kinetics of oxidation of five vicinal, four non-vicinal diols, and one of their monoethers bybis(2,2′-bipyridyl) copper(II) permanganate (BBCP), has been studied. The vicinal diols yielded the products arising out of the glycol bond fission, while the other diols yielded the hydroxycarbonyl compounds. The reaction is first-order with respect to BBCP. Michaelis-Menten type kinetics were observed with respect to the diol. There is no effect of added 2,2′-bipyridine on the reaction. The oxidation of [1,1,2,2-2H4] ethanediol showed the absence of a primary kinetic isotope effect. A mechanism involving a glycol bond fission has been proposed for the oxidation of the vicinal diols. The other diols are oxidised by a hydride-transfer mechanism as are monohydric alcohols.
Volume 135, 2023
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