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

Original 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

English

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.

Keywords

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

Authors

Kula, Karolina; Lapczuk, Agnieszka; Sadowski, Mikolaj; Kras, Jowita; Zawadzinska, Karolina; Demchuk, Oleg M.; Gaurav, Gajendra Kumar; Wroblewska, Aneta; Jasinski, Radomir

Released

1. 12. 2022

Publisher

MDPI

Location

ST ALBAN-ANLAGE 66, CH-4052 BASEL, SWITZERLAND

ISBN

1420-3049

Periodical

MOLECULES

Year of study

23

Number

27

State

Swiss Confederation

Pages count

10

URL

https://www.mdpi.com/1420-3049/27/23/8409

BibTex

@article{BUT182690,
  author="Kula, Karolina and Lapczuk, Agnieszka and Sadowski, Mikolaj and Kras, Jowita and Zawadzinska, Karolina and Demchuk, Oleg M. and Gaurav, Gajendra Kumar and Wroblewska, Aneta and Jasinski, Radomir",
  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",
  journal="MOLECULES",
  year="2022",
  volume="23",
  number="27",
  pages="10",
  doi="10.3390/molecules27238409",
  issn="1420-3049",
  url="https://www.mdpi.com/1420-3049/27/23/8409"
}