Investigation into the Regiochemistry of 1,3-Dipolar Cycloaddition of C,N-Diphenyl Nitrone with Some Vinyl Sulfoximines as Dipolarophile:Theoretical Studies

摘要

The regiochemistry of 1,3-dipolar cycloaddition reactions of C,N-diphenyl nitrone with some vinyl sulfoximines as dipolarophile was investigated using density functional theory (DFT)-based reactivity indexes and activation energy calculations at B3LYP/6-31G(d) level of theory. Analysis of the geometries and bond orders (BOs) at the TS structures associated with the different reaction pathways shows that these 1,3-dipolar cycloaddition reactions occur via an asynchronous concerted mechanism. Analysis of the local electrophilicity and nucleophilicity indexes permits an interpretation about the regioselectivity of these 1,3-dipolar cycloaddition reactions. The theoretical results obtained in the work clearly predict the regiochemistry of the isolated cycloadducts and agree to experimental outcomes.