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Molecules 2018, 23(4), 897; https://doi.org/10.3390/molecules23040897

Radical-Mediated Reactions of α-Bromo Aluminium Thioacetals, α-Bromothioesters, and Xanthates for Thiolactone Synthesis

1
School of Chemistry, Trinity Biomedical Sciences Institute (TBSI), Trinity College Dublin, The University of Dublin, 152-160 Pearse Street, Dublin 2, Ireland
2
CEISAM UMR CNRS 6230, Université de Nantes, UFR des Sciences et des Techniques, 2 rue de la Houssinière, BP 92208, 44322 Nantes CEDEX 3, France
*
Author to whom correspondence should be addressed.
Academic Editors: John C. Walton and Derek J. McPhee
Received: 9 March 2018 / Revised: 3 April 2018 / Accepted: 10 April 2018 / Published: 13 April 2018
(This article belongs to the Special Issue Radical Chemistry)
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Abstract

Thiolactones have attracted considerable attention in recent years as bioactive natural products, lead compounds for drug discovery, molecular probes, and reagents for polymerisation. We have investigated radical-mediated C-C bond forming reactions as a strategy for thiolactone synthesis. Cyclisation of an α-bromo aluminium thioacetal was investigated under radical conditions. It was found that at low temperature, a radical fragmentation and rearrangement process occurs. A putative reaction mechanism involving a previously unreported aluminium templated thiol-ene step for the rearrangement process is presented. Cyclisation reactions of α-bromo thioesters and α-xanthate thioesters under radical mediated conditions furnished the desired thiolactones in moderate yields. View Full-Text
Keywords: radical fragmentation; radical cyclisation; thiyl radical radical fragmentation; radical cyclisation; thiyl radical
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McCourt, R.O.; Dénès, F.; Scanlan, E.M. Radical-Mediated Reactions of α-Bromo Aluminium Thioacetals, α-Bromothioesters, and Xanthates for Thiolactone Synthesis. Molecules 2018, 23, 897.

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