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Anchimeric Assistance in Hydrogen-Atom Transfer to Bromine

Croft, Anna; Easton, Christopher

Description

The free-radical benzylic brominations of series of phenylalanine derivatives and O-phenylalkyi benzoates and N-phenylalkylamides with N-bromosuccinimide exhibit anchimeric assistance by neighbouring ester and amido groups. Rate enhancement occurs through electron donation to the electropositive carbon centre that develops in the transition state of the hydrogen-atom transfer to bromine. The extent of the effect depends on the electron demand at the benzylic position and the electron-donating...[Show more]

CollectionsANU Research Publications
Date published: 2004
Type: Journal article
URI: http://hdl.handle.net/1885/78381
Source: Australian Journal of Chemistry
DOI: 10.1071/CH04058

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