A theoretical study on the regioselectivity of 1,3-dipolar cycloadditions using DFT-based reactivity indexes

被引：160

作者：

Aurell, MJ

Domingo, LR

Pérez, P

Contreras, R

机构：

[1] Univ Valencia, Inst Ciencia Mol, Dept Quim Organ, E-46100 Valencia, Spain

[2] Univ Andres Bello, Fac Ecol & Recursos Nat, Dept Ciencias Quim, Santiago, Chile

[3] Univ Chile, Fac Ciencias, Dept Quim, Santiago, Chile

来源：

TETRAHEDRON | 2004年 / 60卷 / 50期

关键词：

1.3-dipolar cycloadditions; regioselectivity; local electrophilicity; Fukui functions; density functional theory;

D O I：

10.1016/j.tet.2004.09.057

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The regioselectivity for a series of four 1,3-dipolar cycloaddition reactions has been studied using global and local reactivity indexes. The results of the theoretical analysis suggest that for asynchronous cycloadditions associated to polar processes, the regioselectivity is consistently explained by the most favorable two-center interactions between the highest nucleophilic and electrophilic sites of the reagents. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：11503 / 11509

页数：7

共 71 条

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