Bamberger rearrangement

The Bamberger rearrangement is the chemical reaction of N-phenylhydroxylamines with strong aqueous acid, which will rearrange to give 4-aminophenols. It is named for the German chemist Eugen Bamberger (1857–1932).

The Bamberger rearrangement

N-Phenylhydroxylamines are typically synthesized from nitrobenzenes by reduction using rhodium or zinc.

Reaction mechanism

The mechanism of the Bamberger rearrangement proceeds from the monoprotonation of N-phenylhydroxylamine 1. N-protonation 2 is favored, but unproductive. O-protonation 3 can form the nitrenium ion 4, which can react with nucleophiles (H₂O) to form the desired 4-aminophenol 5.

The mechanism of the Bamberger rearrangement

See also

• Friedel–Crafts alkylation-like reactions:
  • Hofmann-Martius rearrangement
  • Fries rearrangement
  • Fischer–Hepp rearrangement

• ;
• ;
• ;