Issue 22, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Chemoselective debenzylation of N-benzyl tertiary amines with ceric ammonium nitrate

Steven D. Bull,a   Stephen G. Davies,*a   Garry Fenton,b   Andrew W. Mulvaney,a   R. Shyam Prasada  and  Andrew D. Smitha  

* Corresponding authors

a The Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, UK
E-mail: steve.davies@chemistry.ox.ac.uk

b Rhône-Poulenc Rorer, Rainham Road South, Dagenham, Essex, UK

Abstract

Treatment of a range of N-benzyl tertiary amines with aqueous ceric ammonium nitrate results in N-debenzylation to afford the corresponding secondary amine. Chemoselective mono-N-debenzylation of N-benzyl tertiary amines is shown to occur in the presence of N-benzyl amides, O-benzyl ethers, O-benzyl esters, O-benzyl phenolates and S-benzyl ethers.

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Article information

DOI
https://doi.org/10.1039/B006852G
Article type
Paper
Submitted
22 Aug 2000
Accepted
15 Sep 2000
First published
30 Oct 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 3765-3774

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Chemoselective debenzylation of N-benzyl tertiary amines with ceric ammonium nitrate

S. D. Bull, S. G. Davies, G. Fenton, A. W. Mulvaney, R. S. Prasad and A. D. Smith, J. Chem. Soc., Perkin Trans. 1, 2000, 3765 DOI: 10.1039/B006852G

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