THEORETICAL AND EXPERIMENTAL STUDY ON THE REGIOSELECTIVITY OF ACRYLONITRILE AND METHYLMETHACRYLATE 1,3-DIPOLAR CYCLOADDITION TO SOME NITRILIMINES-Reference-Cited by-同舟云学术

THEORETICAL AND EXPERIMENTAL STUDY ON THE REGIOSELECTIVITY OF ACRYLONITRILE AND METHYLMETHACRYLATE 1,3-DIPOLAR CYCLOADDITION TO SOME NITRILIMINES

Published:2012-02 Issue:01 Volume:11 Page:99-109
ISSN:0219-6336
Container-title:Journal of Theoretical and Computational Chemistry
language:en
Short-container-title:J. Theor. Comput. Chem.

Author:

MOEINPOUR F.¹,BAKAVOLI M.²,DAVOODNIA A.²,MORSALI A.²

Affiliation:

1. Department of Chemistry, Islamic Azad University, Bandar Abbas Branch, Bandar Abbas, Iran

2. Department of Chemistry, Islamic Azad University, Mashhad Branch, Mashhad, Iran

Abstract

1,3-dipolar cycloaddition between acrylonitrile and methylmethacrylate with two N-(4-bromophenyl)-C-(4-substituted) nitrilimines which were generated in situ afforded the new pyrazoles. The regioselectivity and reactivity of these reactions has been investigated on the basis of density functional theory (DFT)-based reactivity indexes and activation energy calculations. The theoretical 13C NMR chemical shifts of the cycloadducts which were obtained by GIAO method were comparable with the observed values.

Publisher

World Scientific Pub Co Pte Lt

Subject

Computational Theory and Mathematics,Physical and Theoretical Chemistry,Computer Science Applications

Link

https://www.worldscientific.com/doi/pdf/10.1142/S021963361250006X

Reference37 articles.

1. Asymmetric 1,3-Dipolar Cycloaddition Reactions

2. 1,3-Dipolar cycloaddition reaction of 5-substituted pyridazinones with nitrile imines: synthesis of pyrazolo[3,4- d ]pyridazines

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