Characteristics of the two frontier orbital interactions in the Diels-Alder cycloaddition

被引：53

作者：

Spino, C ^{[1
]}

Rezaei, H ^{[1
]}

Dory, YL ^{[1
]}

机构：

[1] Univ Sherbrooke, Dept Chim, Sherbrooke, PQ J1K 2R1, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 03期

关键词：

D O I：

10.1021/jo0353740

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two electron-deficient dienes were reacted with a series of twelve electron-poor and electron-rich dienophiles to give, in some cases, the corresponding Diels-Alder adducts. Clear differences in the roles played by the two frontier orbital interactions emerged. It was demonstrated that in the case of normal Diels-Alder cycloadditions, the FMO theory could predict the relative reactivities between dienophiles, while in the case of inverse-electron demand Diels-Alder reactions, it could not. It was shown that the dissymmetry in electron-rich dienophiles increases their reactivities.

引用

页码：757 / 764

页数：8

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