An experimental and theoretical study of the hetero Diels–Alder reactions between (E)-2-aryl-1-cyano-1-nitroethenes and ethyl vinyl ether: one-step or zwitterionic, two-step mechanism?
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- 作者：Radomir Jasiński (1)
Magdalena Kubik (1)
Agnieszka ?apczuk-Krygier (1)
Agnieszka K?cka (1)
Ewa Dresler (2)
Anna Boguszewska-Czubara (3) - 关键词：Diels–Alder reaction ; Mechanism ; DFT calculations ; Solvent effect ; Electrophilicity
- 刊名：Reaction Kinetics, Mechanisms and Catalysis
- 出版年：2014
- 出版时间：December 2014
- 年：2014
- 卷：113
- 期：2
- 页码：333-345
- 全文大小：565 KB
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26. - 作者单位：Radomir Jasiński (1)
Magdalena Kubik (1)
Agnieszka ?apczuk-Krygier (1)
Agnieszka K?cka (1)
Ewa Dresler (2)
Anna Boguszewska-Czubara (3)
1. Institute of Organic Chemistry and Technology, Cracow University of Technology, Warszawska 24, 31-155, Kraków, Poland
2. Institute of Heavy Organic Synthesis “Blachownia- Energetyków 9, 47-225, K?dzierzyn-Ko?le, Poland
3. Department of Medicinal Chemistry, Medical University of Lublin, Chod?ki 4a, 20-093, Lublin, Poland - ISSN：1878-5204
文摘
The mechanistic aspects of the hetero Diels–Alder reactions between strongly electrophilic (E)-2-aryl-1-cyano-1-nitroethenes and ethyl vinyl ether have been analyzed on the basis of kinetic experimental results as well as quantum chemical simulations of reaction paths. These reactions may theoretically proceed via one step or stepwise, zwitterionic mechanism. It was found that the conversion of addends into adducts carried out via polar, but not zwitterionic mechanism. This is confirmed by kinetic substituent and solvent effects. Subsequently, a?detailed analysis of internal reaction coordinate trajectories shows that?the title reactions?should be considered as examples of “two-stage one-step-cycloadditions?according to Domingo terminology.