The oxidation of some vicinal and non-vicinal diols and two of their monoethers by [bis(trifluoroacetoxy)iodo]benzene (TFAIB) in aqueous
acetic acid solution has been studied. The oxidation of vicinal diols leads to glycol-bond fission. The non-vicinal diols behave like
monohydric alcohols and leads to the formation of hydroxy carbonyl compounds. The reaction is first order in TFAIB and a MichaelisMenten kinetics was obtained with respect to the reductant. The reaction showed a first order dependence on hydrogen-ions. The oxidation
of [1,1,2,2-
2H4]ethandiol exhibited the absence of a kinetic isotope effect. Suitable mechanisms have been proposed.
Key words: diols; hypervalent iodine; oxidation; kinetics; mechanism
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