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14-September-2008 18:38:40 - Bamberger rearrangement The Bamberger rearrangement is the chemical reaction of N-phenylhydroxylamines with strong aqueous acid, which will rearrange to give 4-aminophenols.12 It is named for the German chemist Eugen Bamberger 1857-1932. The Bamberger rearrangement N-Phenylhydroxylamines are typically synthesized from nitrobenzenes by reduction using rhodium3 or zinc4. 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 5.56 The mechanism of the Bamberger rearrangement References ^ Bamberger, E. 1894. Uber das Phenylhydroxylamin. Chem. Ber. 27: 1347 1548-1557. doi:10.1002/cber.18940270276. ^ Harman, R. E. 1955. Chloro-p-benzoquinone. Organic Syntheses 35: 22. also in the Collective Volume 1963 4:148 PDF. ^ Oxley, P. W.; Adger, B. M.; Sasse, M. J.; Forth, M. A. 1989. N-Acetyl-N-phenylhydroxylamine via Catalytic Transfer Hydrogenation of Nitrobenzene using Hydrazine and Rhodium on Carbon. Organic Syntheses 67: 187. also in the Collective Volume 1993 8:16 PDF. ^ Kamm, O. 1925. β-Phenylhydroxylamine. Organic Syntheses 4: 57. 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. Part 4. Rearrangement of sterically hindered phenylhydroxylamines to 4-aminophenols in aqueous sulphuric acid solution. J. Chem. Soc. Perkin Trans. II: 1596-1598. doi:10.1039/P29810000298. ^ George Kohnstam, W. Andrew Petch and D. Lyn H. Williams 1984. Kinetic substituent and isotope effects in the acid-catalysed rearrangement of N-phenylhydroxylamines. Are nitrenium lons involved?. J. Chem. Soc. Perkin Trans. II: 423-427. doi:10.1039/P29840000423. See also Hofmann-Martius rearrangement Retrieved from http://en..org/wiki/Bamberger_rearrangement Categories: Rearrangement reactions | Name reactions Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Français Nederlands 日本語 中文 This page was last modified on 13 September 2008, at 13:45
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