Publication detail
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
Kula, Karolina Lapczuk, Agnieszka Sadowski, Mikolaj Kras, Jowita Zawadzinska, Karolina Demchuk, Oleg M. Gaurav, Gajendra Kumar Wroblewska, Aneta Jasinski, Radomir
English title
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
Type
journal article in Web of Science
Language
en
Original 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 Delta(2)-pyrazoline molecular system. This was the result of a unique CHCl3 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-Delta(2)-pyrazoline was more probable. On the other hand, according to the experimental data, the presented reactions occurred with full regioselectivity.
English 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 Delta(2)-pyrazoline molecular system. This was the result of a unique CHCl3 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-Delta(2)-pyrazoline was more probable. On the other hand, according to the experimental data, the presented reactions occurred with full regioselectivity.
Keywords in English
pyrazoline; pyrazole; nitrocompound; nitrylimine; cycloaddition reaction; molecular electron density theory; synthesis; 3+2 CYCLOADDITION REACTIONS; 1,3-DIPOLAR CYCLOADDITION; PYRAZOLINE DERIVATIVES; AZOMETHINE YLIDES; MECHANISM; REACTIVITY; INSECTICIDES; INDOXACARB; CHEMISTRY; QUANTUM
Released
01.12.2022
Publisher
MDPI
Location
ST ALBAN-ANLAGE 66, CH-4052 BASEL, SWITZERLAND
ISSN
1420-3049
Volume
23
Number
27
Pages count
10
BIBTEX
@article{BUT182690,
author="Karolina {Kula} and Gajendra Kumar {Gaurav},
title="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",
year="2022",
volume="23",
number="27",
month="December",
publisher="MDPI",
address="ST ALBAN-ANLAGE 66, CH-4052 BASEL, SWITZERLAND",
issn="1420-3049"
}