A DFT analysis of the strain-induced regioselective[2+2]cycloaddition of benzyne possessing fused four-membered ring

被引：13

作者：

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, Dept Ciencias Quim, Fac Ecol & Recursos Nat, Santiago 275, Chile

[3] Univ Chile, Fac Ciencias, Dept Quim, Santiago 653, Chile

来源：

LETTERS IN ORGANIC CHEMISTRY | 2005年 / 2卷 / 01期

关键词：

2+2] cycloadditions; benzyne; regioselectivity; angle strain; DFT calculations;

D O I：

10.2174/1570178053399958

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The regioselective [2+2] cycloaddition of a substituted benzyne possessing a fused four-membered ring to a ketene acetal has been theoretically studied. This cycloaddition presents a two-step mechanism that is initiated by the nucleophilic attack to the benzyne to give a zwitterionic intermediate. The analysis performed on the basis of the global and local electrophilicity of reagents correctly explain the observed reactivity and regioselectivity in this system.

引用

页码：68 / 73

页数：6

共 47 条

[1] DFT study of the cycloaddition reactions of strained alkynes [J].