Issue 20, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Reactions of 1-(2-alkoxyphenyl)alkaniminyl radicals

Rino Leardini,a   Hamish McNab,*b   Matteo Minozzi,a   Daniele Nanni,*a   David Reedb  and  Andrew G. Wrightb  

* Corresponding authors

a Dipartimento di Chimica Organica “A Mangini”, Università di Bologna, Viale Risorgimento 4, Bologna, Italy

b Department of Chemistry, The University of Edinburgh, West Mains Road, Edinburgh, UK

Abstract

Genereration of the iminyls 1d and 1e by standard methods in the gas-phase by flash vacuum pyrolysis (FVP), or in solution, respectively, gives rise to 1,3-benzoxazines 18 and 22 by a mechanism which probably involves a 1,6-hydrogen atom translocation. Under FVP conditions, 2-cyanophenol 14 is a major product from 2-alkoxyphenylalkaniminyls 1b–d; the dealkylation is an integral part of the reaction mechanism and not a subsequent reaction of 2-alkoxybenzonitriles, which themselves are only very minor products of the pyrolyses.

Graphical abstract: Reactions of 1-(2-alkoxyphenyl)alkaniminyl radicals

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Article information

DOI
https://doi.org/10.1039/B103181N
Article type
Paper
Submitted
09 Apr 2001
Accepted
22 Aug 2001
First published
27 Sep 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 2704-2710

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Reactions of 1-(2-alkoxyphenyl)alkaniminyl radicals

R. Leardini, H. McNab, M. Minozzi, D. Nanni, D. Reed and A. G. Wright, J. Chem. Soc., Perkin Trans. 1, 2001, 2704 DOI: 10.1039/B103181N

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