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On the Question of the Formation of Nitro-Functionalized 2,4-Pyrazole Analogs on the Basis of Nitrylimine Molecular Systems and 3,3,3-Trichloro-1-Nitroprop-1-Ene.
- Source :
-
Molecules (Basel, Switzerland) [Molecules] 2022 Dec 01; Vol. 27 (23). Date of Electronic Publication: 2022 Dec 01. - Publication Year :
- 2022
-
Abstract
- Experimental and theoretical studies on the reaction between ( E )-3,3,3-trichloro-1-nitroprop-1-ene and N -(4-bromophenyl)-C-arylnitrylimine were performed. It was found that the title process unexpectedly led to 1-(4-bromophenyl)-3-phenyl-5-nitropyrazole instead of the expected Δ <superscript>2</superscript> -pyrazoline molecular system. This was the result of a unique CHCl <subscript>3</subscript> elimination process. The observed mechanism of transformation was explained in the framework of the molecular electron density theory (MEDT). The theoretical results showed that both of the possible channels of [3 + 2] cycloaddition were favorable from a kinetic point of view, due to which the creation of 1-(4-bromophenyl)-3-aryl-4-tricholomethyl-5-nitro-Δ <superscript>2</superscript> -pyrazoline was more probable. On the other hand, according to the experimental data, the presented reactions occurred with full regioselectivity.
- Subjects :
- Models, Molecular
Cycloaddition Reaction
Electrons
Subjects
Details
- Language :
- English
- ISSN :
- 1420-3049
- Volume :
- 27
- Issue :
- 23
- Database :
- MEDLINE
- Journal :
- Molecules (Basel, Switzerland)
- Publication Type :
- Academic Journal
- Accession number :
- 36500503
- Full Text :
- https://doi.org/10.3390/molecules27238409