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Rück-Braun, K.; Priewisch, B., Science of Synthesis, (2007) 31, 1340.
Peroxymonosulfuric acid (H2SO5, Caro's Acid) oxidizes primary arylamines 59 to the corresponding nitrosoarenes 60 (Scheme 31).[71–76] The active oxidant is the peroxymonosulfate ion (HSO5−). Solutions of Caro's acid are prepared from the corresponding sodium or ammonium peroxodisulfates and sulfuric acid prior to use; the amount of active oxygen available being determined by iodometric titration.[77] The oxidation is often carried out in slightly acidic aqueous solution (pH 3–6.5), the pH being adjusted by addition of sodium or potassium carbonate.[71,78] The main byproducts are the corresponding diaryldiazene oxides. In many cases separation of the volatile nitroso compounds can be achieved by steam-distillation.
Meeeee 88 Meeeeeeee ee Meeeeeeeee ee Meee'e Meee[88–88]
M8 | M8 | M8 | M8 | Meeeeeeeee | Meeeeeeeeeeee | Meeee (%) | ee (°M) | Mee |
---|---|---|---|---|---|---|---|---|
M | MM8 | M | M | MeMM, M8M/MeMM, eee eeee, 8–8 e | M | 88 | 88–88 | [88] |
MM8 | M | MM8M | M | M8M, 88°M, 8 e | M (MeMM) | 88 | 888 (eee) | [88] |
M | M | MM8 | M | M8M, 8–88°M, 8 e | M (MeMM) | 88 | 888–888 | [88] |
Me | M | Me | M | eee M8MM8, 88°M, 8 e | M | 88 | 88–88 | [88] |
M | e-Me | M | e-Me | MeMM, 8–88 eee, 88°M | M, M (MeMM) | 88–88 | 88–88 | [88] |
MM8 | M | M | Me | eeeeeee, 88°M, 8 e | M (eeeeeee) | 88 | 888–888 (eee) | [88] |
e M = eeeeeeeeeeeeeeeee; M = eeeee-eeeeeeeeeeee.
Meeeeeeeeeee Meeeeeeee
8,8-Meeeeee-8-eeeeeeeeeeeeee (88, M8 = M8 = Me; M8 = M8 = M); Meeeeee Meeeeeeee:[88]
MMMMMMM: Meeeeeeeeeeeeeeeee eeee ee e eeeeee eeeeeeeee eeeee. Me ee eeee e eeeeeeeee eeeeeeeee, eeeeeeeeee ee eee eeeee eeeee. Meeeeeeee eeeeee eeeeee ee eeeeeee eeeeeeee eeeee ee eee, eee eee eeeeee.
M eeeeeee ee (MM8)8M8M8 (88.8 e, 8.8 eee) eee eeeee M8MM8 (88 e) eee eeeeeee eee 8 e ee 88°M, eeee eeeeee eeee eee (888 e), eeeeee eee eeeeeee eee eeeeeee eeee M8M (8.8 M). 8,8-Meeeeeeeeeeeee (88 e, 88.8 eeee) eee eeeee eee eee eeeeeee eee eeeeeee eee 8 e ee 88°M. Mee eeeeeeeeeee eeee eeeeee eee eeeeeeeee ee eeeeeeeeee, eeeeee eeee M8M, eeeee-eeeeeeeee, eee eeeee ee e eeeeeeeeee (M8M88) ee eeee eee eeeee eeeeeeee; eeeee: 8.88 e (88%); ee 88–88°M.
References
[71] | Meeeee, M. M.; Meeee, M. M.; Meeeee, M. M.; Meeee, M. M.; Meeeeeeeee, M. M.; Meeeeee, M. M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[72] | Meeee, M.; Meeee, M., Meee. Meee. Meee, (8888) 88, 888. |
[73] | Meeee, M., Me.M. Meeeeeeeeeee, Meeeee-Meeeeeeeeee-Meeeeeeeeäe, Müeeeeee, (8888), e 88. |
[74] | Meeeeeee, M. M.; Meeeeee, M. M.; Meeee, M. M.; Meeeeeeee, Me. M.; Meeeeeeeeee, M. M., Mee. Meee. Meee, Mee. Meee., (8888), 8888; Meee. Meee. Meee., (8888) 88, 8888. |
[75] | Meeeee, M. M., Meee. Mee., (8888) 888, 8888. |
[76] | Meeeeee, M. M.; Meeeeeee, M. M.; Meeeeeeee, Me. M.; Meeeeeeeeee, M. M., Mee. Meee. Meee, Mee. Meee., (8888), 888; Meee. Meee. Meee., (8888) 88, 888. |
[77] | Meeeee, M. M.; Meeeeeeeeee, M. M.; Meeeee, M., Mee. M. Mee. Meee., (8888) 8, 8888. |
[78] | Meeeee, M.; Meeee, M. M., M. Meee. Meee., (8888) 888, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 8888.