Abstract
AbstractThe oxidation of 1‐phenyl‐2,2,2‐trifluoroethanol (ROH) with potassium permanganate in 0.2 M aqueous sodium hydroxide solution at 25 °C provides 2,2,2‐trifluoroacetophenone as the sole product. The reaction rate constant, which was measured under pseudo‐first order conditions by following the decrease in substrate concentration as a function of time, was found to be substantially smaller than previously reported. The primary kinetic deuterium isotope effect was measured as k/k = 14·7 ± 1·0. A hydrogen‐transfer mechanism involving significant tunnelling is proposed. The oxidation of 1‐phenylethanol under similar reaction conditions yields acetophenone as the initial product. The kinetic deuterium isotope effect was found to be k/k = 5·2 ± 0·8.
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