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Oxidation of Some Unsaturated Acids by Quinolinium Fluorochromate: A Kinetics and Mechanistic Study

Ajay Sharma, A. Daiya, Om Prakash, S. Agarwal and Vinita Sharma

The oxidation of maleic, fumaric, crotonic and cinnamic acids by quinolinium fluorochromate (QFC) in dimethylsulphoxide (DMSO) leads to the formation of corresponding epoxide. The reaction is of first order with respect to QFC and the acid. Due to non-aqueous nature of the solvents toluene-psulphonic acid (TsOH) was used the source of hydrogen ions. The reaction is catalysed by hydrogen ions. The hydrogen-ion dependence has the form: kobs = a + b [H+]. The oxidation of these acids was studied in nineteen different organic solvents. The solvent effect was analyzed by Kamlet’s and Swain’s multiparametric equations. Solvent effect indicated the importance of the cation-solvating power of the solvent. A mechanism involving a three-centre transition state has been postulated.