Searching for zwitterionic intermediates in Hetero Diels-Alder reactions between methyl α,p-dinitrocinnamate and vinyl-alkyl ethers

被引：63
|
作者：
Jasniski, Radomir [1 ]
机构：
[1] Cracow Univ Technol, Inst Organ Chem & Technol, PL-31155 Krakow, Poland
来源：
COMPUTATIONAL AND THEORETICAL CHEMISTRY | 2014年 / 1046卷
关键词：
Hetero Diels-Alder reaction; Zwitterionic mechanism; Nitroalkene; DFT study; QUANTITATIVE CHARACTERIZATION; CYCLOADDITION; REACTIVITY; DFT; CYCLOPENTADIENE; COMPETITION;
D O I：
10.1016/j.comptc.2014.08.002
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
DFT calculations indicate that reactions of methyl alpha,p-dinitrocinnamate with vinyl-alkyl ethers are of a polar nature, and zwitterionic structures may arise during their course. However, these zwitterions are beyond of cycloadditions paths. On the other hand, HDA reactions of addents carried out according to "two-stage one-step" cycloaddition mechanism. It should be also remarked, that the M062x functional overestimates activation energies. (C) 2014 Elsevier B.V. All rights reserved.
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页码：93 / 98
页数：6
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