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Allylic halogenation of unsaturated amino acids

Easton, Christopher; Edwards, Alison; McNabb, Stephen; Merrett, Martin; O'Connell, Jenny; Simpson, Gregory Wayne; Simpson, Jamie S; Willis, Anthony

Description

A range of dehydro amino acid derivatives has been prepared and subjected to halogenation using either molecular bromine or chlorine, or NBS. Allylic halogenation of the unsaturated amino acid side chains occurs through radical bromination with NBS. The procedure is complementary to treatment with chlorine, which also affords allyl halides. This latter and unusual reaction is shown through a deuterium labelling study to proceed via an ionic mechanism. The choice of NBS or chlorine for allyl...[Show more]

CollectionsANU Research Publications
Date published: 2003
Type: Journal article
URI: http://hdl.handle.net/1885/88367
Source: Organic and Biomolecular Chemistry
DOI: 10.1039/b303719c

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