Investigation of arene–arene interaction in stereoselective MCPBA epoxidation

Abstract

Effect of arene–arene interaction in stereoselective MCPBA epoxidation was investigated using 5,6-dimethyl-2-phenyl-3a,4,7,7a-tetrahydroisoindole-1,3-diones 1. From the good correlation between the stereoselectivity of the products and Hammett’s coefficients of para-substituents (σ_P) on the phenyl group, it was found that polar/π interaction between the phenyl group and MCPBA is the main interaction for controlling the stereoselectivity in the reaction. Other arene–arene interactions, charge-transfer complexation and edge-to-face interaction, were assumed to be much weaker than polar/π interaction in this reaction.