Why do electron-deficient dienes react rapidly in diels-alder reactions with electron-deficient ethylenes? A density functional theory analysis

被引：48
|
作者：
Domingo, LR [1 ]
机构：
[1] Univ Valencia, Inst Ciencia Mol, E-46100 Valencia, Spain
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 23期
关键词：
cycloaddition; density functional calculations; electrophilic addition; electron-deficient compounds; reaction mechanisms;
D O I：
10.1002/ejoc.20040522
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Diels-Alder reaction of the electron-deficient (ED) dimethyl 2,3-dimethylenesuccinate with two electron-rich (ER) and two ED ethylenes has been studied at the B3LYP/6-31G* level-of theory. The analysis of the geometry and electronic structure of the transition state of the reaction with the ED dimethyl 2-methylenemalonate along with the analysis of the global and local electrophilicity indices of the reagents provide an explanation of the participation of this ED diene as nucleophile against powerful electrophiles in polar Diels-Alder reactions. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
引用
收藏
页码：4788 / 4793
页数：6
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