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

作　　者：Moeinpour, Farid 

机构地区：[1]Department of Chemistry, Faculty of Sciences, Islamic Azad University, Bandar Abbas Branch, Bandar Abbas 7915893144, lran

出　　处：《Chinese Journal of Chemistry》2011年第7期1429-1433,共5页中国化学（英文版）

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 reac- tions occur via an asynchronous concerted mechanism. Analysis of the local electrophilicity and nucleophilicity in- dexes 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.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 reac- tions occur via an asynchronous concerted mechanism. Analysis of the local electrophilicity and nucleophilicity in- dexes 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.

关 键 词：regioselectivity CYCLOADDITION density functional calculations 

分 类 号：O626.3[理学—有机化学] TQ252.1[理学—化学]