References. Bamberger, E. 'Uber das Phenylhydroxylamin' (Abstract). 27: 1347 & 1548–1557. (also in the Collective Volume (1963) 4:148 (PDF)).
W.; Adger, B. M.; Sasse, M. J.; Forth, M. 'N-Acetyl-N-phenylhydroxylamine via Catalytic Transfer Hydrogenation of Nitrobenzene using Hydrazine and Rhodium on Carbon'. (also in the Collective Volume (1993) 8:16 (PDF)).
(also in the Collective Volume (1941) 1:445 (PDF)). Sone, Takaaki; Hamamoto, Kazuhiro; Seiji, Yoshiyuki; Shinkai, Seiji; Manabe, Osamu (1981). 'Kinetics and mechanisms of the Bamberger rearrangement.
Rearrangement of sterically hindered phenylhydroxylamines to 4-aminophenols in aqueous sulphuric acid solution'. Perkin Trans. II: 1596–1598. George Kohnstam, W. Andrew Petch and D. Williams (1984). 'Kinetic substituent and isotope effects in the acid-catalysed rearrangement of N-phenylhydroxylamines.
Bamberger Rearrangement Reaction
Are nitrenium lons involved?' Perkin Trans.
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Bamberger Rearrangement
The reaction occurred in the presence of cell extract and H 2 but did not occur in cell extract-free controls. From spectroscopic data, the product of 2,4-dihydroxylamino-6-nitrotoluene rearrangement was identified as either 2-amino-4-hydroxylamino-5-hydroxyl- 6-nitrotoluene (4-amino-6-hydroxylamino-3-methyl-2-nitrophenol) or 2-hydroxylamino-4-amino-5-hydroxyl-6-nitrotoluene (6-amino-4-hydroxylamino-3-methyl-2-nitrophenol). Acid-catalyzed rearrangement of 2,4-dihydroxylamino-6-nitrotoluene resulted in a single product, which after derivatization, was identical to a derivatized product from cell extracts. Acid-catalyzed Bamberger rearrangement oc curs with the hydroxyl addition para to the participating hydroxylamine, indicating that the 2-amino-4-hydroxylamino-5-hydroxyl-6-nitrotoluene (4-amino-6-hydroxylamino-3-methyl-2-nitrophenol) was the product isolated form cell extracts. This product was also confirmed in whole cell systems that had been fed TNT. Following derivatization of the culture broth, a product was isolated that was identical to those isolated from crude cell extracts and acid catalysis experiments.
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