Published Online: 15 SEP 2010
Copyright © 2010 John Wiley & Sons, Inc. All rights reserved.
Comprehensive Organic Name Reactions and Reagents
How to Cite
2010. Bamberger Rearrangement. Comprehensive Organic Name Reactions and Reagents. 45:191–194.
- Published Online: 15 SEP 2010
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Intermolecular rearrangement of N-phenylhydroxylamines in acidic aqueous solution to afford the corresponding 4-aminophenols, e.g., in aqueous sulfuric acid, is generally referred to as the Bamberger rearrangement. It has been reported that in this rearrangement the hydroxyl group is introduced into the aromatic ring via a nucleophilic attack of a hydrosulfate ion on the anilenium ion, which is generated by the heterolytic N-O bond cleavage of O-protonated N-phenylhydroxylamine. It has been found that alkoxy, halogen, phenoxy are incorporated into the aromatic ring when the rearrangement of N-phenylhydroxylamine is carried out in nucleophilic solvents.
- hydrosulfate ion;