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).

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-aminofenol 5.^[5]^[6]

Lihat pula

Penataan ulang Hofmann-Martius

Referensi

↑ E. Bamberger. Uber das Phenylhydroxylamin. Chem. Ber. 1894. Vol. 27. hlm. 1347 & 1548–1557. doi:10.1002/cber.18940270276.
↑ R. E. Harman. Chloro-p-benzoquinone. Organic Syntheses. 1955. Vol. 35. hlm. 22. (also in the Collective Volume (1963) 4:148 (PDF)).
↑ 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. Vol. 67. hlm. 187. (also in the Collective Volume (1993) 8:16 (PDF)).
↑ O. Kamm. β-Phenylhydroxylamine. Organic Syntheses. 1925. Vol. 4. hlm. 57. (also in the Collective Volume (1941) 1:445 (PDF)).
↑ 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. hlm. 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. hlm. 423–427. doi:10.1039/P29840000423.

Sumber dan atribusi

Konten artikel ini diadaptasi dari Wikipedia bahasa Indonesia, revisi 27963267 (2025-10-13T22:25:04Z), yang tersedia berdasarkan lisensi Creative Commons Atribusi-BerbagiSerupa (CC BY-SA). Mohon gunakan konten ini secara bijak serta sesuai dengan ketentuan lisensi yang berlaku.

[1] E. Bamberger. Uber das Phenylhydroxylamin. Chem. Ber. 1894. Vol. 27. hlm. 1347 & 1548–1557. doi:10.1002/cber.18940270276.

[2] R. E. Harman. Chloro-p-benzoquinone. Organic Syntheses. 1955. Vol. 35. hlm. 22. (also in the Collective Volume (1963) 4:148 (PDF)).

[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. Vol. 67. hlm. 187. (also in the Collective Volume (1993) 8:16 (PDF)).

[4] O. Kamm. β-Phenylhydroxylamine. Organic Syntheses. 1925. Vol. 4. hlm. 57. (also in the Collective Volume (1941) 1:445 (PDF)).

[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. hlm. 1596–1598. doi:10.1039/P29810000298.

[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. hlm. 423–427. doi:10.1039/P29840000423.

[1]

[2]

[3]

[4]

[5]

[6]