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Chem Commun (Camb). 2002 Feb 7;(3):216-7.

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

Author information

1
Laboratoire de Chimie Moléculaire Organique-UMR 6517, Boite 562-Faculté des Sciences St Jérome, Université d' Aix-Marseille III, Av. Escadrille Normandie-Niemen 13397, Marseille, France.

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.

PMID:
12120373

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