A DFT study on the 1,3-dipolar cycloaddition reactions of C-(hetaryl) nitrones with methyl acrylate and vinyl acetate

被引：41
|
作者：
Merino, Pedro [1 ]
Tejero, Tomas
Chiacchio, Ugo
Romeo, Giovanni
Rescifina, Antonio
机构：
[1] Univ Zaragoza, Dept Quim Organ, Inst Ciencia Mat Aragon, CSIC, E-50009 Zaragoza, Spain
[2] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy
[3] Univ Messina, Dipartimento Farm Chim, I-98168 Messina, Italy
来源：
TETRAHEDRON | 2007年 / 63卷 / 06期
关键词：
D O I：
10.1016/j.tet.2006.11.073
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The 1,3-dipolar cycloaddition of C-(hetaryl) nitrones with electron-poor and electron-rich alkenes is rationalized. The energetics of the cycloaddition reactions have been investigated through molecular orbital calculations at the B3LYP/6-31-G(d) theory level. By studying different reaction channels and reagent conformations the regio- and stereochemical preferences of the reaction are discussed. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1448 / 1458
页数：11
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