A theoretical study of the mechanism and stereoselectivity of the Diels-Alder cycloaddition between difluoro-2-methylencyclopropane and furan

被引：14
|
作者：
Nacereddine, Abdelmalek Khorief [1 ]
Yahia, Wassila [1 ]
Sobhi, Chafia [1 ]
Djerourou, Abdelhafid [1 ]
机构：
[1] Univ Badji Mokhtar Annaba, Fac Sci, Dept Chim, Lab Synth & Biocatalyse Organ, Annaba 23000, Algeria
来源：
TETRAHEDRON LETTERS | 2012年 / 53卷 / 43期
关键词：
Diels-Alder cycloaddition; Stereoselectivity; Molecular mechanism; DFT calculations;
D O I：
10.1016/j.tetlet.2012.08.067
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A theoretical study of the molecular mechanism and stereoselectivity of the Diels-Alder cycloaddition reaction between difluoro-2-methylencyclopropane and furan has been carried out at the B3LYP/6-31G** level of theory. The calculation of activation and reaction energies indicates that the 3-endo cycloadduct is favored both kinetically and thermodynamically, which is in agreement with the experimental data. Analysis of the bond order and charge transfer in the transition states shows that this reaction takes place via a synchronous-concerted mechanism. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5784 / 5786
页数：3
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