班贝尔格尔重排反应

班伯格重排反应（Bamberger重排反应）是N-芳基羟胺在强酸水溶液作用下重排为对氨基苯酚的反应。^[1]^[2]它以德国化学家尤金·班伯格（Eugen Bamberger，1857-1932）的名字命名。当对位有取代基时，产物为相应的醌醇。

N-芳基羟胺一般由铑^[3]或锌^[4]还原相应的芳香硝基化合物制备。

反应机理

首先发生对羟胺（1）氮和氧的质子化。N-质子化与O-质子化的产物（2与3）互为平衡，前者容易发生，但只有3可以失水，进一步转化为氮鎓离子（4），作亲电试剂与水分子结合生成产物（5）。^[5]^[6]

Bamberger重排反应机理

参见

参考资料

^ Bamberger, E. Uber das Phenylhydroxylamin. Chem. Ber. 1894, 27: 1347 & 1548–1557 [2008-09-13]. doi:10.1002/cber.18940270276. （原始内容存档于2020-10-07）.
^ Harman, R. E. Chloro-p-benzoquinone. Organic Syntheses. 1955, 35: 22 [2008-09-13]. （原始内容存档于2013-06-07）. (also in the Collective Volume (1963) 4:148 (PDF) （页面存档备份，存于互联网档案馆）).
^ Oxley, P. W.; Adger, B. M.; Sasse, M. J.; Forth, M. A. N-Acetyl-N-phenylhydroxylamine via Catalytic Transfer Hydrogenation of Nitrobenzene using Hydrazine and Rhodium on Carbon. Organic Syntheses. 1989, 67: 187 [2008-09-13]. （原始内容存档于2012-02-06）. (also in the Collective Volume (1993) 8:16 (PDF) （页面存档备份，存于互联网档案馆）).
^ Kamm, O. β-Phenylhydroxylamine. Organic Syntheses. 1925, 4: 57 [2008-09-13]. （原始内容存档于2012-10-13）. (also in the Collective Volume (1941) 1:445 (PDF) （页面存档备份，存于互联网档案馆）).
^ Sone, Takaaki; Hamamoto, Kazuhiro; Seiji, Yoshiyuki; Shinkai, Seiji; Manabe, Osamu. 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. 1981: 1596–1598. doi:10.1039/P29810000298.
^ George Kohnstam, W. Andrew Petch and D. Lyn H. Williams. Kinetic substituent and isotope effects in the acid-catalysed rearrangement of N-phenylhydroxylamines. Are nitrenium lons involved?. J. Chem. Soc. Perkin Trans. II. 1984: 423–427. doi:10.1039/P29840000423.

[bamberger1894-1] Bamberger, E. Uber das Phenylhydroxylamin. Chem. Ber. 1894, 27: 1347 & 1548–1557 [2008-09-13]. doi:10.1002/cber.18940270276. （原始内容存档于2020-10-07）.

[os1955-2] Harman, R. E. Chloro-p-benzoquinone. Organic Syntheses. 1955, 35: 22 [2008-09-13]. （原始内容存档于2013-06-07）. (also in the Collective Volume (1963) 4:148 (PDF) （页面存档备份，存于互联网档案馆）).

[oxley1989-3] Oxley, P. W.; Adger, B. M.; Sasse, M. J.; Forth, M. A. N-Acetyl-N-phenylhydroxylamine via Catalytic Transfer Hydrogenation of Nitrobenzene using Hydrazine and Rhodium on Carbon. Organic Syntheses. 1989, 67: 187 [2008-09-13]. （原始内容存档于2012-02-06）. (also in the Collective Volume (1993) 8:16 (PDF) （页面存档备份，存于互联网档案馆）).

[kamm1925-4] Kamm, O. β-Phenylhydroxylamine. Organic Syntheses. 1925, 4: 57 [2008-09-13]. （原始内容存档于2012-10-13）. (also in the Collective Volume (1941) 1:445 (PDF) （页面存档备份，存于互联网档案馆）).

[sone1981-5] Sone, Takaaki; Hamamoto, Kazuhiro; Seiji, Yoshiyuki; Shinkai, Seiji; Manabe, Osamu. 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. 1981: 1596–1598. doi:10.1039/P29810000298.

[kohnstam1984-6] George Kohnstam, W. Andrew Petch and D. Lyn H. Williams. Kinetic substituent and isotope effects in the acid-catalysed rearrangement of N-phenylhydroxylamines. Are nitrenium lons involved?. J. Chem. Soc. Perkin Trans. II. 1984: 423–427. doi:10.1039/P29840000423.

[1]

[2]

[3]

[4]

[5]

[6]