Regiospecific formation of the nitromethyl-substituted 3-phenyl-4,5- dihydroisoxazole via [3 + 2] cycloaddition
Authors:
- Barbara Mirosław,
- Dmytro Babyuk,
- Agnieszka Łapczuk-Krygier,
- Agnieszka Kącka-Zych,
- Oleg M. Demchuk,
- Radomir Jasiński
Abstract
5-(Nitromethyl)-3-phenyl-4,5-dihydroisoxazole was obtained as a product of a high-yielding [3 ? 2] cycloaddition reaction of in situ-generated benzonitrile N-oxide and 3-nitroprop-1-ene. For the first time, the regiochemistry of this reaction was unambiguously proven by X-ray structural analysis. The quantum-chemical calculation performed at the M06-2X/6-31G(d) (PCM) theoretical level affords a basis for explaining the course of reaction as well as the nature of transition states. Next, further DFT calculations together with spectral data shed light on structural aspects of the product.
- Record ID
- CUT815172361a0649e48d2233d143762a9b
- Publication categories
- ;
- Author
- Journal series
- Monatshefte für Chemie, ISSN 0026-9247, e-ISSN 1434-4475
- Issue year
- 2018
- Vol
- 149
- No
- 10
- Pages
- 1877-1884
- Other elements of collation
- rys.; tab.; Bibliografia (na s.) - 1883-1884; Bibliografia (liczba pozycji) - 45; Oznaczenie streszczenia - Abstr.; Numeracja w czasopiśmie - Vol. 149, Iss. 10
- Keywords in English
- isoxazole, Nitrocompounds, 3-nitroprop-1-ene, DFT calculations, [3+2] cycloaddition
- DOI
- DOI:10.1007/s00706-018-2227-6 Opening in a new tab
- URL
- https://link.springer.com/article/10.1007/s00706-018-2227-6 Opening in a new tab
- Related project
- Kwantowochemiczne studia reakcji cykloaddycji. . Project leader at PK: , ,
Działalność statutowa - Language
- eng (en) English
- License
- Score (nominal)
- 25
- Publication indicators
- Citation count
- 27
- Additional fields
- Indeksowana w: Web of Science, Scopus
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUT815172361a0649e48d2233d143762a9b/
- URN
urn:pkr-prod:CUT815172361a0649e48d2233d143762a9b
* 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.