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Bamberger Rearrangement

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr045

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Bamberger Rearrangement. Comprehensive Organic Name Reactions and Reagents. 45:191–194.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

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.

Keywords:

  • hydrosulfate ion;
  • N-phenylhydroxylamine;
  • isoquinolones;
  • pyridines