The Genesis of the Reversible Radical Addition–Fragmentation–Transfer of Thiocarbonylthio Derivatives from the Barton–McCombie Deoxygenation: A Brief Account and Some Mechanistic Observations

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Contents Vol 59(10)

doi:10.1071/CH06263

The Genesis of the Reversible Radical Addition–Fragmentation–Transfer of Thiocarbonylthio Derivatives from the Barton–McCombie Deoxygenation: A Brief Account and Some Mechanistic Observations*

Samir Z. Zard

Laboratoire de Synthèse Organique associé au CNRS (UMR 7652), Département de Chimie, Ecole Polytechnique, 91128 Palaiseau, France. Email: zard@poly.polytechnique.fr





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Australian Journal of Chemistry 59(10) 663–668 http://dx.doi.org/10.1071/CH06263
Submitted: 25 July 2006 Accepted: 14 September 2006 Published online: 30 October 2006

Abstract

The observations and reasoning leading to the discovery of the degenerative transfer of xanthates and related thiocarbonylthio derivatives are briefly described. A few synthetic applications are presented, and the consequences on the emergence of the RAFT and MADIX polymerization technologies as well as some mechanistic aspects are briefly discussed.

^* This paper is dedicated with respect and affection to the memory of Derek H. R. Barton.