Liquid-phase oxidation of cyclohexene and of tetralin by N2O in the presence of onium salts under mild experimental conditions

Cyclohexene and tetralin can be oxidized to a slight extent by N2O in the presence of quaternary ammonium salt promoters under mild experimental conditions. In non-polar solutions, the higher yields of the oxidations of cyclohexene and tetralin are influenced by the donor–acceptor properties of the solvents. The changes in the IR spectrum of N2O lend further support to the assumption that ion-pair interactions between the solvated oxidant and the onium salts result in an enhanced rate of O-transfer from the oxidant. Onium-decavanadate ion-pair complexes are more effective promoters than simple onium salts.

Graphical abstractCyclohexene and tetralin can be oxidized by N2O in the presence of quaternary ammonium salts (Q+X−) under mild experimental conditions (70 °C, atmospheric pressure). The kinetical observations and the changes in the IR spectrum of N2O support the ion-pair interactions between the oxidant and the onium salts which result in an enhanced rate of O-transfer from the oxidant.Figure optionsDownload full-size imageDownload as PowerPoint slide