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Oxidation of Aliphatic Primary Alcohols by Tetraethylammonium Chlorochromate: A Kinetic and Mechanistic Approach

K. Vadera, M. Patel, S. Vyas, P. Purohit, P. Pancharia and Pradeep K. Sharma

The oxidation of nine aliphatic primary alcohols by tetraethylammonium chlorochromate (TEACC) in dimethylsulphoxide leads to the formation of corresponding aldehydes. The reaction is first order with respect to both; TEACC and the alcohol. The reaction is catalysed by hydrogen ions. The hydrogen-ion dependence has the form: kobs = a + b [H+]. The oxidation of [1,1-2H2]ethanol (MeCD2OH) exhibits a substantial primary kinetic isotope effect. The reaction has been studied in nineteen different organic solvents. The solvent effect was analysed using Taft's and Swain's multiparametric equations. The rate of oxidation is susceptible to both; polar and steric effects of the substituents. A suitable mechanism has been proposed.