Issue 9, 2011
From the journal:

Organic & Biomolecular Chemistry

Translocation versus cyclisation in radicals derived from N-3-alkenyl trichloroacetamides

M. Luisa Marin,*a   Ramon J. Zaragoza,*b   Miguel A. Miranda,a   Faïza Diabac  and  Josep Bonjochc  

* Corresponding authors

a Instituto de Tecnología Química-Departamento de Química (UPV-CSIC), Avda de los Naranjos s/n, Valencia, Spain
E-mail: marmarin@qim.upv.es
Fax: + 34963877809
Tel: + 34963877815

b Departamento de Quimica Organica, Universidad de Valencia, Dr Moliner 50, Burjassot, Valencia, Spain
E-mail: ramon.j.zaragoza@uv.es

c Laboratori de Química Orgànica, Facultat de Farmàcia, Institut de Biomedicina (IBUB), Universitat de Barcelona, Av., Joan XXIII s/n, Barcelona, Spain

Abstract

Under radical reaction conditions, two different and competitive reaction pathways were observed for N-(α-methylbenzyl)trichloroacetamides with a N-3-cyclohexenyl substituent: 1,4-hydrogen translocation and radical addition to a double bond. However, for radicals with an acyclic alkenyl side chain, the direct cyclisation process was exclusively observed. The dichotomy between translocation and direct radical cyclisation in these substrates has been theoretically studied using density functional theory (DFT) methods at the B3LYP/6-31G** computational level.

Graphical abstract: Translocation versus cyclisation in radicals derived from N-3-alkenyl trichloroacetamides

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Article information

DOI
https://doi.org/10.1039/C0OB01228A
Article type
Paper
Submitted
21 Dec 2010
Accepted
17 Feb 2011
First published
18 Feb 2011

Org. Biomol. Chem., 2011,9, 3180-3187

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Translocation versus cyclisation in radicals derived from N-3-alkenyl trichloroacetamides

M. L. Marin, R. J. Zaragoza, M. A. Miranda, F. Diaba and J. Bonjoch, Org. Biomol. Chem., 2011, 9, 3180 DOI: 10.1039/C0OB01228A

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