Penataan ulang Bamberger

Penataan ulang Bamberger merupakan reaksi kimia antara N-fenilhidroksilamina dengan asam kuat, membentuk senyawa 4-aminofenol.[1][2] Nama reaksi ini berasal dari kimiawan Jerman Eugen Bamberger (1857–1932).

The Bamberger rearrangement
The Bamberger rearrangement

N-fenilhidroksilamina umumnya disintesis dari nitrobenzena melalui reduksi menggunakan rodium[3] atau seng.[4]

Mekanisme reaksi

Mekanisme penataan ulang Bamberger dimulai dari monoprotonasi N-fenilhidroksilamina 1. N-protonasi 2 lebih difavoritkan, tetapi ia tidak akan menghasilkan apa-apa. O-protonasi 3 dapat menghasilkan ion nitrenium 4, yang kemudian dapat bereaksi dengan nukleofil (H2O) dan membentuk senyawa 4-aminophenol 5.[5][6]

The mechanism of the Bamberger rearrangement
The mechanism of the Bamberger rearrangement

Referensi

  1. ^ Bamberger, E. (1894). "Uber das Phenylhydroxylamin". Chem. Ber. 27: 1347 & 1548–1557. doi:10.1002/cber.18940270276. 
  2. ^ Harman, R. E. (1955). "Chloro-p-benzoquinone". Organic Syntheses. 35: 22.  (also in the Collective Volume (1963) 4:148 (PDF)).
  3. ^ 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)).
  4. ^ Kamm, O. (1925). "β-Phenylhydroxylamine". Organic Syntheses. 4: 57.  (also in the Collective Volume (1941) 1:445 (PDF)).
  5. ^ 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. 
  6. ^ 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. 

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