Surf Wiki
Save to docs
general/rearrangement-reactions

From Surf Wiki (app.surf) — the open knowledge base

Bamberger rearrangement

Bamberger rearrangement

The Bamberger rearrangement is the chemical reaction of 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

The starting phenylhydroxylamines are typically synthesized by the transfer hydrogenation of nitrobenzenes using rhodium or zinc catalysts.

One application is in the synthesis of .

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

References

References

  1. Harman, R. E.. (1955). "Chloro-p-benzoquinone".
  2. Bamberger, E.. (1894). "Ueber die Reduction der Nitroverbindungen". [[Chemische Berichte]].
  3. Bamberger, E.. (1894). "Ueber das Phenylhydroxylamin". Chemische Berichte.
  4. (1989). "N-Acetyl-N-Phenylhydroxylamine Via Catalytic Transfer Hydrogenation of Nitrobenzene Using Hydrazine and Rhodium on Carbon". Organic Syntheses.
  5. Kamm, O.. (1925). "β-Phenylhydroxylamine".
  6. (1981). "Kinetics and Mechanisms of the Bamberger Rearrangement. Part 4. Rearrangement of Sterically Hindered Phenylhydroxylamines to 4-Aminophenols in Aqueous Sulphuric Acid Solution". [[Journal of the Chemical Society, Perkin Transactions 2]].
  7. (1984). "Kinetic Substituent and Isotope Effects in the Acid-Catalysed Rearrangement of N-Phenylhydroxylamines. Are Nitrenium Ions Involved?". Journal of the Chemical Society, Perkin Transactions 2.
Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

rearrangement-reactions name-reactions
Want to explore this topic further?

Ask Mako anything about Bamberger rearrangement — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report