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The kinetics of oxidation of alpha-hydroxy acids (mandelic, lactic and glycolic) with a recently developed new mild Cr(VI) regent quinolinium fluorochromate (QFC) has been investigated in perchloric acid medium. First-order depedence with respect to [oxidant] is observed. Increase in [substrate] increases the rate proportionally. The acidity dependence is fractional order throughout the entire range of acidities studied. Decrease in dielectric constant of the medium increases the oxidation rate considerably. Kinetic solvent isotope effect studies indicate a pre-equilibrium fast proton transfer. Absence of polymerization with acrylonitrile rules out a free radical mechanism. An intermediate formed between protonated oxidant and substrate decomposes in a slow rate-limiting step giving the products.
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2261--2266
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Bibliogr. 28 poz., rys., tab.
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Bibliografia
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bwmeta1.element.baztech-article-BAR1-0001-0044