On the mechanism of the synthesis of nitrofunctionalised Δ2-pyrazolines via [3+2] cycloaddition reactions between α-EWG-activated nitroethenes and nitrylimine TAC systems
Authors:
- Agnieszka Fryźlewicz,
- Aleksandra Olszewska,
- Karolina Zawadzińska,
- Przemysław Woliński,
- Karolina Kula,
- Agnieszka Kącka-Zych,
- Agnieszka Łapczuk-Krygier,
- Radomir Jasiński
Abstract
We investigated the reactivity of different substituted nitrylimine-type three atom components (TACs) in [3+2] cycloaddition (32CAs) reactions with electrophilically activated nitroethenes within molecular electron density theory (MEDT). In parallel research, the molecular mechanism of the considered transformation was examined through analysis of all possible reaction channels and full optimization of all critical structures. In particular, the existence of zwitterionic intermediates on reaction paths was verified. On the basis of the bonding evolution theory (BET), the mechanism of the 32CA reaction between C,N-diphenylnitrylimine and (E)-2-phenyl-1-cyano-1-nitroethene should be treated as a one-step two-stage mechanism.
- Record ID
- CUT5f62423e5b104b92b29642d3c75117c7
- Publication categories
- ;
- Author
- Journal series
- Organics , ISSN , e-ISSN 2673-401X, Annual
- Issue year
- 2022
- Vol
- 3
- No
- 1
- Pages
- 59-76
- Other elements of collation
- rys.; tab.; wykr.; Bibliografia (na s.) - 74-76; Bibliografia (liczba pozycji) - 46; Oznaczenie streszczenia - Abstr.; Numeracja w czasopiśmie - Vol. 3, Iss. 1, Spec. Iss.
- Substantive notes
- Special Issue: Chemistry of Heterocycles
- Keywords in English
- [3+2] cycloaddition, nitrilimine, nitroalkene, Δ2-pyrazoline, molecular electron density theory (MEDT)
- DOI
- DOI:10.3390/org3010004 Opening in a new tab
- URL
- https://www.mdpi.com/2673-401X/3/1/4 Opening in a new tab
- Language
- eng (en) English
- License
- Score (nominal)
- 5
- Score source
- journalList
- Score
- Publication indicators
- = 6
- Citation count
- 6
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUT5f62423e5b104b92b29642d3c75117c7/
- URN
urn:pkr-prod:CUT5f62423e5b104b92b29642d3c75117c7
* 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.