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Anchimeric Assistance in Hydrogen-Atom Transfer to Bromine

Date

2004

Authors

Croft, Anna
Easton, Christopher

Journal Title

Journal ISSN

Volume Title

Publisher

CSIRO Publishing

Abstract

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 ability of the neighbouring group.

Description

Keywords

Keywords: Alcohols; Amino acids; Bromine; Derivatives; Electrochemistry; Esters; Free radical reactions; Halogenation; Hydrogen; Paramagnetic resonance; Rate constants; Anchimeric assistance; Ionic processes; Substituents; Transition states; Aromatic hydrocarbons

Citation

Source

Australian Journal of Chemistry

Type

Journal article

Book Title

Entity type

Access Statement

License Rights

DOI

10.1071/CH04058

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