The Bamberger rearrangement is the chemical reaction of phenylhydroxylamines with strong aqueous acid , which will rearrange to give 4-aminophenols.[ 1] It is named for the German chemist Eugen Bamberger (1857–1932).[ 2] [ 3]
The Bamberger rearrangement
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 ] .
^ Harman, R. E. (1955). "Chloro-p-benzoquinone" (PDF) . Organic Syntheses . 35 : 22 ; Collected Volumes , vol. 4, p. 148 .
^ Bamberger, E. (1894). "Ueber die Reduction der Nitroverbindungen" . Chemische Berichte . 27 (2): 1347–1350. doi :10.1002/cber.18940270229 .
^ Bamberger, E. (1894). "Ueber das Phenylhydroxylamin" . Chemische Berichte . 27 (2): 1548–1557. doi :10.1002/cber.18940270276 .
^ Oxley, P. W.; Adger, B. M.; Sasse, M. J.; Forth1, M. A. (1989). "N-Acetyl-N-Phenylhydroxylamine Via Catalytic Transfer Hydrogenation of Nitrobenzene Using Hydrazine and Rhodium on Carbon". Organic Syntheses . 67 : 187. 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 )