Asian Journal of Research in Chemistry

The oxidation of fumaric, maleic, crotonic and cinnamic acids by Benzimidazolium dichromate (BIDC) in dimethylsulphoxide (DMSO) leads to the formation of corresponding epoxide. The reaction is of first order with respect to BIDC and the unsaturated acid. p-toluene sulphonic acid (TsOH) was used as a source of hydrogen ions due to non-aqueous nature of the solvents. 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.