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

Abstract

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.