Oxidation of nine primary aliphatic alcohols by pyridinium bromochromate (PBC) leads to the formation of corresponding aldehydes. The reaction is of overall second order, and of first order with respect to the each reactant. The reaction is promoted by hydrogen ions; the hydrogen-ion dependence has the formkobs=c+d[H+]. The oxidation of [1, 1-2H2] ethanol (MeCD2OH) exhibited a substantial primary kinetic isotope effect. The reaction was studied in nineteen organic solvents and the effect of solvent was analysed using Taft's and Swein's multiparametric equations. The oxidation is susceptible to both the polar and steric effects of the substituents. A suitable mechanism has been proposed.
Volume 134, 2022
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