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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Anchimeric Assistance in Hydrogen-Atom Transfer to Bromine

Anna K. Croft and Christopher J. Easton

Australian Journal of Chemistry 57(7) 651 - 654
Published: 07 July 2004

Abstract

The free-radical benzylic brominations of series of phenylalanine derivatives and O-phenylalkyl 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.

https://doi.org/10.1071/CH04058

© CSIRO 2004

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