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Please login to access the full content or check if you have access via31.21.1.90 Method 90: Oxidation of Primary Amines Using Peroxysulfuric Acid or Peroxydisulfuric Acid
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Aitken, K. M.; Aitken, R. A., Science of Synthesis, (2007) 31, 1290.
Peroxysulfuric acid (Caro's acid) was first used to oxidize aniline to nitrobenzene in the late 19th century.[400] It can be generated from potassium or ammonium persulfate in acidic solution. Peroxydisulfuric acid is an anhydride of sulfuric and peroxysulfuric acid and may be prepared by oxidation of oleum with ozone or hydrogen peroxide. It is a very powerful oxidant that oxidizes even very electron-poor aromatic amines. For that reason, it has been used mainly in the preparation of polynitrobenzenes such as 172–174 (Scheme 140).[401–403] Other examples are given in Table 21.[319,367,404–410]
Meeeee 888 Meeeeeeee ee Meeeeeee Meeeee Meeee Meeeeeeeeeeeeeee Meee[888–888]
Meeee 88 Meeeeeeeee Meeee Meeeeeeeeeeeee Meee ee Meeeeeeeeeeeeeee Meee[888,888,888–888]
Meeeeeee | Meeeeeee | Meeeeeeeee | Meeeeee | Meeeee (%) | Mee |
---|---|---|---|---|---|
8-eeeeee-8-eeeeeeeeeeee | (MM8)8M8M8, eeeee M8MM8 | 8°M ee ee, 88 e | 8,8-eeeeeeeeeeeeee | 88 | [888] |
eeeeeee-8,8-eeeeeee | M8MM8 | 8°M, 88 eee | 8-eeeeeeeeeeee | 88 | [888] |
8-eeeeeeeeeeee | (MM8)8M8M8, eeeee M8MM8 | 88–88°M, 88 e | 8,8-eeeeeeeeeeeeee | 88–88 | [888] |
8-eeeee-8,8-eeeeeeeeeeeeeee-8,8-eeeeeeeeeeeee | eeeee M8MM8, 88% M8M8 | 8°M, 8 e, eeee ee, 8 e | 8,8-eeeeeeee-8-eeeeeeeeeeee-8,8-eeeeeeeeeeeee | 88 | [888] |
8,8,8-eeeeeeeeeeeeeeee | M8MM8 | ee, 88 e | 8,8,8-eeeeeeeee-8-eeeeeeeeeeee | e.e. | [888] |
8-eeeeee-8,8,8,8-eeeeeeeeeeeeeeeee | eeeee (88% MM8), 88% M8M8 | 88°M, 88 e | eeeeeeeeeeeeeeeee | e.e. | [888] |
8,8′,8,8′,8,8′,8,8′-eeeeeeeeeeeeeeeee-8,8′-eeeeeee | eeeee, 88% M8M8 | eeeeeeee ee M8M8 ee 8°M; 88 e, ee | eeeeeeeeeeeeeeeee | 88 | [888] |
8-eeeeee-8,8,8-eeeeeeeeeeeeeee | 888% M8MM8, 88% M8M8 | 88°M, 88 e | 8,8,8,8-eeeeeeeeeeeeeeeee | 88 | [888] |
8-eeeeee-8,8,8,8-eeeeeeeeeeeeeeeee | eeeee M8MM8, eeeee (88% MM8), 88% M8M8 | eeeeeeee ee M8M8 ee 8°M; ee, eeeeeeeee | eeeeeeeeeeeeeeeee | 88 | [888] |
e e.e. = eee eeeeeeee.
Meeeeeeeeeee Meeeeeeee
8,8,8,8-Meeeeeeeeeeeeeeee (888):[888]
M eeee ee 8-eeeeee-8,8,8-eeeeeeeeeeeeeee (888 e, 8 eee) ee M8MM8 (e 8.88 e·eM−8; 8 M) eee eeeeeee eeeeeeeeee ee ee eee M8M8M8 (8888 e, 8.88 eee) ee M8MM8 (e 8.88 e·eM−8; 8 M) eee eeeee eee ee eeee. Mee eeeeeee eeeeee eeeeee eeeeee, eeeeeeeeee ee eeeee 888°M, eee e eeeee eeeee eeeee eee eeee. Mee eeeee eeee eeeeeeeeeee eee eeeeee eeeeee. Mee eeeeeee eee eeeeeee ee eeeee ee ee eeeeeeeee. Mee eeeee eee eeeeeeeee ee eeeeeeeeee, eeeeee eeee 88% M8MM8, eeee M8M, eee eee eeeee; eeeee: 888 e (88%); ee 888–888°M; eeeeeeeeeeeeeeeee (MMMe8) eeee e eeeee eeeeeee; ee 888.8°M.
Meeeeeeeeeeeeeee (888):[888]
MMMMMMM: Meeee eeeeeeeee eeeeee eeeeeeeee eee eee eeeee eee ee eeeeee eeeeeeeee ee e eeeeee ee eeeee.
Meeeeeeeeeeeeeeee (8.88 e, 8.8 eeee) eee eeeeeeeee ee 88% eeeee (88 eM). M8 eee eee eeeeeee eeee eee eeeeeee eeee eee 88 e ee ee. Mee eeeeeee eee eeee eeeeee eeee M8 eee eeeeeeeee eeee MM8Me8 (8 × 888 eM). Mee eeeeeeee eeeeeeee eeee eeeee (MeMM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee e eeeeee eeeee; eeeee: 8.88 e (88%); eeeeeeeeeeeeeeeee (eee MMMe8) eeee eeeeee eeeeee eeeeee; ee 888–888°M.
8-Meeeee-8,8,8,8,8-eeeeeeeeeeeeeeeee (888):[888]
M eeee ee 8-eeeeee-8,8,8,8-eeeeeeeeeeeeeeeee (8.88 e, 8.8 eeee) ee eeeee (88 eM; 88% MM8) eee eeeeeee ee 8°M eee 88% M8M8 (8.8 eM) eee eeeee eeeeeeee eeee 88 eee (eeeeeeeeeee <88°M). Meeee eeeeeeee ee 88°M eee 88 e, eee eeeeeee eee eeeeeeeee eeee MM8Me8 eee eee eeeeeeee eeee eeeee (MeMM8) eee eeeeeeeeeeee ee eeee eee eeeee eeeeeee; eeeee: 8.88 e (88%); eeeeeeeeeeeeeeeee [MMe8 (MMMMMMM: eeeee)] eeee eeee eeeeeeee; eeeee: 8.88 e (88%); ee 888–888°M; 88M MMM (MMMe8, δ eeee MMMe8): −888.88.
References
[319] | Meeeee, M. M.; Meeeeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[367] | Meee, M. M.; Meeeeee, M. M., M. Meee. Mee., (8888) 888, 8888. |
[400] | Meee, M., Meeee. Meee., (8888) 88, 888. |
[401] | Meeeeeee, M. M., Meee. Meee. Meee. Meee-Mee, (8888) 88, 888. |
[402] | Meeeee, M. M.; Meeeeee, M. M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 888. |
[403] | Meeeeee, M. M.; Meeeee, M. M.; Meeeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[404] | Meeeeeeee, M.; Müeeee, M., Mee. Meeee. Meee. Mee., (8888) 88, 8888. |
[405] | Meee, M. M.; Meeeeeeeee, M., Mee. Meeee. Meee. Mee., (8888) 88, 8888. |
[406] | Meeeeee, M. M.; Meee, M. M.; Meeeee, M.; Meeeeee, M. M.; Meeeeee, M., M. Mee. Meee., (8888) 8, 888. |
[407] | Meeeee, M.; Meeeeee, M.; Meeeeeeee, M.; Meeee, M., Meeeeeeeeee. Meee, Meee M, (8888) 88, 8888. |
[408] | Meeeeee, M. M.; Meeeee, M. M.; Meeeee, M. M.; Meee, M. M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[409] | Meeeeee, M. M.; Meeeee, M. M.; Meeeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[410] | Meeeeee, M. M.; Meeeeeeee, M. M.; Meeeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.