One-step versus two-step mechanism of Diels-Alder reaction of 1-chloro-1-nitroethene with cyclopentadiene and furan
Authors:
- Radomir Jasiński
Abstract
DFT computational study shows that Diels-Alder (DA) reactions of 1-chloro-1-nitroethene with cyclopentadiene and furan have polar nature. However, their mechanism is substantially different. In particular, 1-chloro-1-nitroethene react with cyclopentadiene according to one-step mechanism. In the same time, more favourable channel associated with the P-DA reaction between furan and 1-chloro-1-nitroethene is a domino process, that comprises an initial hetero-Diels-Alder reaction yielding a [2 + 4] cycloadduct, which experiences a subsequent [3,3] sigmatropic shift to yield the expected formal [4 + 2] cycloadduct. This is a consequence of more polar nature of reaction, due to higher nucleophilicity of furan in comparison to cyclopentadiene.
- Record ID
- CUT1ef89d0d1c534499b05512e58599ebd8
- Publication categories
- ;
- Author
- Journal series
- Journal of Molecular Graphics & Modelling, ISSN 1093-3263, e-ISSN 1873-4243
- Issue year
- 2017
- Vol
- 75
- Pages
- 55-61
- Other elements of collation
- rys.; schem.; tab.; wykr.; Bibliografia (na s.) - 60-61; Bibliografia (liczba pozycji) - 38; Oznaczenie streszczenia - Abstr.; Numeracja w czasopiśmie - Vol. 75
- Keywords in English
- Diels-Alder reaction, nitroalkenes, DFT study, mechanism
- DOI
- DOI:10.1016/j.jmgm.2017.04.008 Opening in a new tab
- URL
- http://www.sciencedirect.com/science/article/pii/S1093326316302881 Opening in a new tab
- Language
- eng (en) English
- Score (nominal)
- 25
- Additional fields
- Indeksowana w: Web of Science, Scopus
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUT1ef89d0d1c534499b05512e58599ebd8/
- URN
urn:pkr-prod:CUT1ef89d0d1c534499b05512e58599ebd8
* presented citation count is obtained through Internet information analysis, and it is close to the number calculated by the Publish or PerishOpening in a new tab system.