Oxidation of the aniline–styrene epoxide- p -toluenesulfonic acid ternary system in polar solvents: Trends and mechanism

Investigation of the kinetics of oxygen absorption by the aniline–styrene epoxide-p-toluenesulfonic acid ternary system (TS) in an acetonitrile solution led to a simple equation for the oxidation rate: V TS = k[aniline]0 • [epoxide]0[acid]1 at [aniline], [epoxide] ≫ [acid], k = 0.77 × 10–3s–1, and 343 K. The data obtained indicated that a complex of the three starting reagents formed before oxidation. In a mixed solvent containing tert-butanol, the dependence of V TS on its composition was extremum. A scheme was suggested that explained the change in the dependence V TS = k′[aniline]–0.63[epoxide]0.86[acid]1 in the mixed solvent by the decomposition of the complex in the presence of alcohol.