Stereoselectivity and kinetics of [4 + 2] cycloaddition reaction of cyclopentadiene to para-substituted E-2-arylnitroethenes
Тип публикации: Journal Article
Дата публикации: 2011-03-23
scimago Q3
wos Q3
БС2
SJR: 0.318
CiteScore: 4.1
Impact factor: 1.8
ISSN: 08943230, 10991395
Organic Chemistry
Physical and Theoretical Chemistry
Краткое описание
In spite of diversified electrophilicity of E-2-arylnitroethenes, their [4 + 2] cycloaddition reactions with cyclopentadiene leads to the corresponding 6-endo-aryl-5-exo-nitronorbornenes and 6-exo-aryl-5-endo-nitronorbornenes as the only reaction products. Stereoselectivity, substituent and solvent effects, and activation parameters, suggest that these reactions occur via a synchronous concerted mechanism on both competing pathways. The experimental results obtained are consistent with the data from B3LYP/6-31G(d) calculations. Due to high electrophilicity of E-2-arylnitroethenes, the reactions studied should be considered as polar [4 + 2] cycloadditions. Copyright © 2011 John Wiley & Sons, Ltd.
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Jasiński R., Kwiatkowska M., Barański A. Stereoselectivity and kinetics of [4 + 2] cycloaddition reaction of cyclopentadiene to para-substituted E-2-arylnitroethenes // Journal of Physical Organic Chemistry. 2011.
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Jasiński R., Kwiatkowska M., Barański A. Stereoselectivity and kinetics of [4 + 2] cycloaddition reaction of cyclopentadiene to para-substituted E-2-arylnitroethenes // Journal of Physical Organic Chemistry. 2011.
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TY - JOUR
DO - 10.1002/poc.1853
UR - https://doi.org/10.1002/poc.1853
TI - Stereoselectivity and kinetics of [4 + 2] cycloaddition reaction of cyclopentadiene to para-substituted E-2-arylnitroethenes
T2 - Journal of Physical Organic Chemistry
AU - Jasiński, Ryszard
AU - Kwiatkowska, Magdalena
AU - Barański, Andrzej
PY - 2011
DA - 2011/03/23
PB - Wiley
SN - 0894-3230
SN - 1099-1395
ER -
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@article{2011_Jasiński,
author = {Ryszard Jasiński and Magdalena Kwiatkowska and Andrzej Barański},
title = {Stereoselectivity and kinetics of [4 + 2] cycloaddition reaction of cyclopentadiene to para-substituted E-2-arylnitroethenes},
journal = {Journal of Physical Organic Chemistry},
year = {2011},
publisher = {Wiley},
month = {mar},
url = {https://doi.org/10.1002/poc.1853},
doi = {10.1002/poc.1853}
}