Fully selective synthesis of spirocyclic-1,2-oxazine N-Oxides via non-catalysed Hetero Diels-Alder reactions with the participation of cyanofunctionalysed conjugated nitroalkenes
Authors:
- Przemysław Woliński,
- Agnieszka Kącka-Zych,
- Aneta Wróblewska,
- Ewelina Wielgus,
- Rafał Dolot,
- Radomir Jasiński
Abstract
Hetero Diels-Alder (HDA) reactions with the participation of E-2-aryl-1-cyano-1-nitroethenes and methylenecyclopentane were evaluated on the basis of experimental as well as quantumchemical data. It was found that contrary to most known HDA reactions, title processes are realised under non-catalytic conditions and with full regiocontrol. The DFT study shows, without any doubt, the polar but single-step reaction mechanism. Deeper exploration using Bonding Evolution Theory (BET) techniques gives a clear image of the sequences of electron density reorganisation along the reaction coordinate. The first C4-C5 bond is created in phase VII by merging two monosynaptic basins, while the second O1-C6 bond is created in the last phase by a donation of the nonbonding electron density of O1 to C6. Based on the research, we can conclude that the analysed reaction proceeds according to a two-stage one-step mechanism.
- Record ID
- CUT36e4ca9da97d45e18b846c7bc2774a5c
- Publication categories
- ;
- Author
- Journal series
- Molecules, ISSN , e-ISSN 1420-3049, Biweekly
- Issue year
- 2023
- Vol
- 28
- No
- 12
- Pages
- [1-15]
- Article number
- 4586
- Other elements of collation
- rys.; schem.; tab.; Bibliografia (na s.) - 13-15; Bibliografia (liczba pozycji) - 66; Oznaczenie streszczenia - Abstr.; Numeracja w czasopiśmie - Vol. 28, Iss. 12
- Substantive notes
- This article belongs to the Special Issue: Recent Progress in Heteroorganic Chemistry
- Keywords in English
- Diels-Alder, nitroalkenes
- ASJC Classification
- DOI
- DOI:10.3390/molecules28124586 Opening in a new tab
- URL
- https://www.mdpi.com/1420-3049/28/12/4586 Opening in a new tab
- Language
- eng (en) English
- License
- Score (nominal)
- 140
- Score source
- journalList
- Score
- Publication indicators
- Citation count
- 3
- Additional fields
- Indeksowana w: Web of Science, Scopus
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUT36e4ca9da97d45e18b846c7bc2774a5c/
- URN
urn:pkr-prod:CUT36e4ca9da97d45e18b846c7bc2774a5c
* 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.