Issue 3, 2002
From the journal:

Chemical Communications

Tandem radical and non-radical reactions mediated with thiols—a new method of cleavage of allylic amines

Michèle P. Bertrand,a   Stéphanie Escoubet,a   Stéphane Gastaldia  and  Vitaliy I. Timokhinb  

a Laboratoire de Chimie Moléculaire Organique – UMR 6517, Boite 562 – Faculté des Sciences St Jéome, Université d’Aix-Marseille III, Av. Escadrille Normandie–Niemen, Marseille Cedex 20, France

b Department of Physical Chemistry, Institute of Physical Chemistry, National Academy of Sciences of Ukraine, 3A Naukova Street, Lviv, Ukraine

Abstract

Thiyl radical promotes the isomerisation of allylic amines into enamines via two consecutive hydrogen atom abstraction steps, and the subsequent polar addition of the corresponding thiol to the enamine results in the cleavage of the C–N bond via a thioaminal intermediate: this reaction provides a mild, metal-free methodology for the deprotection of allylated primary and secondary amines.

Graphical abstract: Tandem radical and non-radical reactions mediated with thiols—a new method of cleavage of allylic amines

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Article information

DOI
https://doi.org/10.1039/B109781D
Article type
Communication
Submitted
26 Oct 2001
Accepted
03 Dec 2001
First published
08 Jan 2002

Chem. Commun., 2002, 216-217

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Tandem radical and non-radical reactions mediated with thiols—a new method of cleavage of allylic amines

M. P. Bertrand, S. Escoubet, S. Gastaldi and V. I. Timokhin, Chem. Commun., 2002, 216 DOI: 10.1039/B109781D

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