Abstract
The oxidation of maleic, fumaric, crotonic and cinnamic acids by tributylammonium chlorochromate (TBACC) in dimethylsulphoxide (DMSO) leads to the formation of corresponding epoxide. The reaction is of first order with respect to TBACC. A Michaelis-Menten type of kinetics are observed w.r.t. the acids. Due to non-aqueous nature of the solvents, toluene-p-sulphonic acid (TsOH) was used as 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.
Sign-in/Register to access full text options 
Free) 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
