Bamberger rearrangement
From Infogalactic: the planetary knowledge core
The Bamberger rearrangement is the chemical reaction of N-phenylhydroxylamines with strong aqueous acid, which will rearrange to give 4-aminophenols.[1][2][3] It is named for the German chemist Eugen Bamberger (1857–1932).
N-Phenylhydroxylamines are typically synthesized from nitrobenzenes by reduction using rhodium[4] or zinc.[5]
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.[6][7]
References
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