Issue 10, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Amines as leaving groups in nucleophilic aromatic substitution reactions. Part 5.1 Substitution vs.N-oxide formation in the reaction of N-n-butyl-2,6-dinitroaniline with hydroxide ions

Elba I. Buján,*a   A. Irene Cañasa  and  Rita H. de Rossia  

* Corresponding authors

a Instituto de Investigaciones en Fisicoquímica de Córdoba, INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba. Ciudad Universitaria, 5000 Córdoba, Argentina
E-mail: elba@dqo.fcq.unc.edu.ar
Fax: 54-351-4333030

Abstract

A kinetic study of the reaction of N-n-butyl-2,6-dinitroaniline 1 with NaOH was carried out in 10% 1,4-dioxane–water at 25 °C, giving 2,6-dinitrophenol 2 and 7-nitro-2-n-propyl-1H-benzimidazole 3-oxide 3 in ratios depending on the HO−concentration. The rate constant for the formation of 2 is second order in HO− concentration while that of 3 is first order then, the relative amount of 2 ∶ 3 formed increases with HO−. A mechanism involving the formation of a σ complex by addition of HO− to an unsubstituted position of the aromatic ring is proposed for 2,6-dinitrophenol formation. The mechanism suggested for the formation of the N-oxide requires the deprotonation of the substrate.

Graphical abstract: Amines as leaving groups in nucleophilic aromatic substitution reactions. Part 5.1 Substitution vs.N-oxide formation in the reaction of N-n-butyl-2,6-dinitroaniline with hydroxide ions

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Article information

DOI
https://doi.org/10.1039/B103412J
Article type
Paper
Submitted
17 Apr 2001
Accepted
25 Jul 2001
First published
11 Sep 2001

J. Chem. Soc., Perkin Trans. 2, 2001, 1973-1977

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Amines as leaving groups in nucleophilic aromatic substitution reactions. Part 5. Substitution vs.N-oxide formation in the reaction of N-n-butyl-2,6-dinitroaniline with hydroxide ions

E. I. Buján, A. I. Cañas and R. H. de Rossi, J. Chem. Soc., Perkin Trans. 2, 2001, 1973 DOI: 10.1039/B103412J

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