Issue 8, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Metal-assisted reactions. Part 29.1 Structure and hydrogenolysis of C–N bonds in derivatives of aromatic amines. Bond length and electronegativity changes from X-ray crystallographic data

Amadeu, F. Brigas,a   William Clegg,b   Christopher J. Dillon,c   Custodia F. C. Fonsecaac  and  Robert A. W. Johnstone*c  

* Corresponding authors

a UCEH, Campus de Gambelas, Universidade do Algarve, Faro, Portugal

b Department of Chemistry, University of Newcastle, Newcastle-upon-Tyne, UK

c Department of Chemistry, University of Liverpool, Liverpool, UK

Abstract

Pseudosaccharyl and phenyltetrazolyl derivatives 1–6 were prepared with the aim of weakening the originally strong C–N bond in aromatic amines and facilitating its hydrogenolysis. Structural analyses of the amines 1–6 by 1H and 13C NMR spectroscopy and X-ray diffraction methods have revealed major changes in C–N bond lengths on derivatization as a result of changes in conjugation. These changes are discussed in relation to the observed reactivity of compounds 1–6 towards catalytic and non-catalytic C–N bond hydrogenolysis.

Graphical abstract: Metal-assisted reactions. Part 29.1 Structure and hydrogenolysis of C–N bonds in derivatives of aromatic amines. Bond length and electronegativity changes from X-ray crystallographic data

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Article information

DOI
https://doi.org/10.1039/B102571F
Article type
Paper
Submitted
20 Mar 2001
Accepted
12 Jun 2001
First published
09 Jul 2001

J. Chem. Soc., Perkin Trans. 2, 2001, 1315-1324

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Metal-assisted reactions. Part 29. Structure and hydrogenolysis of C–N bonds in derivatives of aromatic amines. Bond length and electronegativity changes from X-ray crystallographic data

A. F. Brigas, W. Clegg, C. J. Dillon, C. F. C. Fonseca and R. A. W. Johnstone, J. Chem. Soc., Perkin Trans. 2, 2001, 1315 DOI: 10.1039/B102571F

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