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Oxidation of some Unsaturated Acids by Quinolinium Dichromate: A Kinetics and Mechanistic Study

Manjari Sharma, U. Soni, Ptsrk Prasad Rao, Om Prakash and Pradeep K. Sharma

The oxidation of maleic, fumaric, crotonic and cinnamic acids by quinolinium dichromate (QDC) in dimethylsulphoxide (DMSO) leads to the formation of corresponding epoxide. The reaction is of first order with respect to QDC and the acid. Due to non-aqueous nature of the solvents toluene-p-sulphonic 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.