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2011 | 9 | 6 | 1008-1018
Tytuł artykułu

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

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
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. [...]
Wydawca

Czasopismo
Rocznik
Tom
9
Numer
6
Strony
1008-1018
Opis fizyczny
Daty
wydano
2011-12-01
online
2011-09-27
Twórcy
  • Institute of Organic Chemistry and Technology, Cracow University of Technology, 31155, Cracow, Poland, radomir@chemia.pk.edu.pl
  • 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
Bibliografia
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Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-011-0088-5
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