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Journal
2011 | 9 | 6 | 1008-1018
Article title

A B3LYP/6-31G(d) study of Diels-Alder reactions between cyclopentadiene and (E)-2-arylnitroethenes

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Abstracts
EN
The B3LYP/6-31G(d) simulations of competing CDA and HDA reactions between cyclopentadiene and (E)-2-arylnitroethenes prove that regardless of the medium polarity, the processes leading to respective 5-nitro-6-aryl-bicyclo-[2,2,0]-hept-2-enes 3,4 (paths A and B) should be most favoured, and the more electrophilic (E)-2-(p-nitrophenyl)-nitroethene should be more reactive than the less electrophilic (E)-2-(p-methoxyphenyl)-nitroethene. Asymmetry of the transition complexes on the favoured pathways increases with increase of medium polarity, but not sufficiently to enforce the zwitterionic mechanism. Analysis of competing pathways leading to HDA adducts proves that not all these compounds can be formed directly from the adducts. In particular, on the path C, the initially formed 5-nitro-6-aryl-bicyclo-[2,2,0]-hept-2-enes 3 is converted to 2-phenyl-4-aza-5-oxy-bicyclo-[3,4,0]-nona-3,7-diene N-oxides 5 as a result of a [3.3]-sigmatropic shift. On the paths D–F leading to 2-phenyl-4-aza-5-oxy-bicyclo-[3,4,0]-nonadienes N-oxides 6–8, the reaction proceeds according to a one-step mechanism. [...]
Publisher

Journal
Year
Volume
9
Issue
6
Pages
1008-1018
Physical description
Dates
published
1 - 12 - 2011
online
27 - 9 - 2011
Contributors
  • Institute of Organic Chemistry and Technology, Cracow University of Technology, 31155, Cracow, Poland, radomir@chemia.pk.edu.pl
author
  • Faculty of Organic Chemistry and Technology, Ivanovo State University of Chemistry and Technology, 153000, Ivanovo, Russian Federation
  • Institute of Organic Chemistry and Technology, Cracow University of Technology, 31155, Cracow, Poland
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Document Type
Publication order reference
Identifiers
YADDA identifier
bwmeta1.element.-psjd-doi-10_2478_s11532-011-0088-5
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