Issue 9, 2011

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

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

Article information

Article type
Paper
Submitted
21 Dec 2010
Accepted
17 Feb 2011
First published
18 Feb 2011

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

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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