Intramolecular Aromatic Nucleophilic Substitution of the Benzimidazole-Activated Nitro Group

2003 ◽  
Vol 5 (25) ◽  
pp. 4795-4798 ◽  
Author(s):  
Tomasz Fekner ◽  
Judith Gallucci ◽  
Michael K. Chan
Keyword(s):  
Nucleophilic Substitution ◽  
Nitro Group ◽  
Aromatic Nucleophilic Substitution

scholarly journals 4,6-Dichloro-5-Nitrobenzofuroxan: Different Polymorphisms and DFT Investigation of Its Reactivity with Nucleophiles

2021 ◽  
Vol 22 (24) ◽  
pp. 13460
Author(s):  
Elena Chugunova ◽  
Nurgali Akylbekov ◽  
Alexey Dobrynin ◽  
Alexander Burilov ◽  
Carla Boga ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Nucleophilic Substitution ◽  
Nitro Group ◽  
Kinetic Data ◽  
Aromatic Nucleophilic Substitution ◽  
X Ray ◽  
Nucleophilic Reactivity ◽  
Amino Derivatives ◽  
Torsional Angles

This research focuses on the X-ray structure of 4,6-dichloro-5-nitrobenzofuroxan 1 and of some of its amino derivatives (4a, 4e, 4g, and 4l) and on DFT calculations concerning the nucleophilic reactivity of 1. We have found that by changing the solvent used for crystallization, it is possible to obtain 4,6-dichloro-5-nitrobenzofuroxan (1) in different polymorphic structures. Moreover, the different torsional angles observed for the nitro group in 1 and in its amino derivatives (4a, 4e, 4g, and 4l) are strictly dependent on the steric hindrance of the substituent at C-4. DFT calculations on the course of the nucleophilic substitution confirm the role of the condensed furoxan ring in altering the aromaticity of the carbocyclic frame, while chlorine atoms strongly influence the dihedral angle and the rotational barrier of the nitro group. These results corroborate previous observations based on experimental kinetic data and give a deep picture of the reaction with amines, which proceeds via a “non-aromatic” nucleophilic substitution.

5-Nitroisoxazoles in SNAr Reactions: Access to Polysubstituted Isoxazole Derivatives

2021 ◽  
Author(s):  
Dmitry A. Vasilenko ◽  
Sevastian E. Dronov ◽  
Dzianis U. Parfiryeu ◽  
Kirill S. Sadovnikov ◽  
Kseniya N. Sedenkova ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Nitro Group ◽  
Aromatic Nucleophilic Substitution ◽  
Isoxazole Ring ◽  
Isoxazole Derivatives

An efficient protocol for straightforward functionalization of isoxazole ring via the reactions of aromatic nucleophilic substitution of nitro group with various nucleophiles has been elaborated. The method is featured with...

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