[3+2] Cycloaddition of diaryldiazomethanes with (E)-3,3,3-trichloro-1-nitroprop-1-ene: An experimental, theoretical and structural study
Authors:
- Karolina Kula,
- Joanna Dobosz,
- Radomir Jasiński,
- Agnieszka Kącka-Zych,
- Agnieszka Łapczuk-Krygier,
- Barbara Mirosław,
- Oleg M. Demchuk
Abstract
The participation of different diaryldiazomethanes as three-atom components (TACs) in [3 + 2] cycloaddition reactions with (E)-3,3,3-trichloro-1-nitroprop-1-ene was analysed. All of the examined reactions occur with full regioselectivity, leading to respective 3,3-diaryl-4-trichloromethyl-5-nitro-D1pyrazolines. Contrary to other known nitro-D1-pyrazolines, these products do not decompose via the N2and/or HNO2 extrusion. At the same time, their spontaneous dehydrochlorination process was unexpectedly observed. This is clearly a rare case of the HCl-elimination from trichloromethylated heterocycles which running under mild conditions. Moreover, the [3 + 2] cycloaddition reaction between diphenyldiazomethane and (E)-3,3,3-trichloro-1-nitroprop-1-ene has been theoretically studied using Molecular Electron Density Theory.
- Record ID
- CUTdcdec7327ad5411a8e21964f835fb148
- Publication categories
- ;
- Author
- Journal series
- Journal of Molecular Structure, ISSN 0022-2860, e-ISSN 1872-8014
- Issue year
- 2020
- Vol
- 1203
- Pages
- [1-10]
- Article number
- 127473
- Other elements of collation
- schem.; tab.; Bibliografia (na s.) - 9-10; Bibliografia (liczba pozycji) - 52; Oznaczenie streszczenia - Abstr.; Numeracja w czasopiśmie - Vol. 1203
- Keywords in English
- [3+2] cycloaddition, density functional theory, molecular electron density theory, nitroalkene, pyrazoline
- DOI
- DOI:10.1016/j.molstruc.2019.127473 Opening in a new tab
- URL
- https://www.sciencedirect.com/science/article/pii/S0022286019315820 Opening in a new tab
- Related project
- Kwantowochemiczne studia reakcji cykloaddycji. . Project leader at PK: , ,
Działalność statutowa - Language
- eng (en) English
- Score (nominal)
- 70
- Publication indicators
- Citation count
- 41
- Additional fields
- Indeksowana w: Web of Science, Scopus
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUTdcdec7327ad5411a8e21964f835fb148/
- URN
urn:pkr-prod:CUTdcdec7327ad5411a8e21964f835fb148
* 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.