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 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 fenhexamid [fr].

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
The mechanism of the Bamberger rearrangement

See also


This page was last updated at 2024-04-16 11:34 UTC. Update now. View original page.

All our content comes from Wikipedia and under the Creative Commons Attribution-ShareAlike License.


Top

If mathematical, chemical, physical and other formulas are not displayed correctly on this page, please useFirefox or Safari