Bamberger rearrangement
Source: Wikipedia, the free encyclopedia.
The Bamberger rearrangement is the
aqueous acid, which will rearrange to give 4-aminophenols.[1] It is named for the German chemist Eugen Bamberger (1857–1932).[2][3]
The starting phenylhydroxylamines are typically synthesized by the transfer hydrogenation of nitrobenzenes using rhodium[4] or zinc[5] 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
See also
- Friedel–Crafts alkylation-like reactions:
- Hofmann–Martius rearrangement
- Fries rearrangement
- Fischer–Hepp rearrangement
- Wallach rearrangement
- Bamberger triazine synthesis — same inventor
References
- ^ Harman, R. E. (1955). "Chloro-p-benzoquinone" (PDF). Organic Syntheses. 35: 22; Collected Volumes, vol. 4, p. 148.
- .
- .
- doi:10.15227/orgsyn.067.0187.)
{{cite journal}}: CS1 maint: numeric names: authors list (link - ^ Kamm, O. (1925). "β-Phenylhydroxylamine". Organic Syntheses. 4: 57; Collected Volumes, vol. 1, p. 445. (download PDF)
- .
- .