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Rück-Braun, K.; Priewisch, B., Science of Synthesis, (2007) 31, 1341.
The oxidation of substituted anilines by peracetic acid, or a mixture of glacial acetic acid and 30% hydrogen peroxide, is another convenient method for the preparation of nitrosobenzenes.[81] This approach is especially useful in the case of 2,6-disubstituted anilines 63, where better yields of the corresponding nitrosoarenes 64 can often be obtained employing peracetic acid (Scheme 33)[81–83] rather than Caro's acid. The reactions are carried out at room temperature or by gently heating the reaction mixture up to 80°C; however, when the substrates are highly hindered the reaction at room temperature may require up to 14 days to complete. Even so, several 3,5-disubstituted 4-nitrosobenzenesulfonic acids, valuable as spin traps, can be prepared by this method.[82,83]
Meeeee 88 Meeeeeeee ee Meeeeeeeee ee Meeeeeeee Meee[88–88]
| M8 | M8 | M8 | Meeeeeeeee | Meeeeeeeeeeee | Meeee (%) | eee (°M) | Mee |
|---|---|---|---|---|---|---|---|
| Me | M | Me | ee, 88 e | M (MeMM) | 88 | 888.8–888 | [88] |
| Me | MM8Me | Me | MeMMe, ee, 88 e | M | 88 | e.e. | [88] |
| Me | MM8Me | Me | MeMMe, 88°M, 8 e, ee, 8 e | M | 88 | e.e. | [88] |
| Me | MM8M | Me | MeMMe, ee, 88 e | M (MeMM) | 88e | >888°M | [88] |
e e.e. = eee eeeeeeee.
e M: Meeeeeeeeeeeeee eeee eeeeeeee eeeeee; M: Meeeeeeeeeeeeeeee.
e Meeeeeee ee eee eeeeee eeee.
Mee eee eeeeeeeee ee eeeeeeee-eeeeeeeeee eeeeeeeeee 88 eee 88 ee eeeeeeeeeeeee 88 eee 88, eeeeeeeeeeee, eee eee ee eeeeeeeeeeeeeeeeeeeee eeee, eeeeeeeee eeee eeeeeeeeeeeeeee eeeeeeeee eee 88 ee 88% eeeeeeee eeeeeeee, eee ee eeeeeeeeeeee (Meeeee 88).[88,88]
Meeeee 88 Meeeeeeee ee Meeeeeee-Meeeeeeeee Meeeeeeeee ee Meeeeeeeeeeeeeeeeeeee Meee[88,88]
Meeeeeeeeeee Meeeeeeee
Meeeee 8,8-Meeeeeee-8-eeeeeeeeeeeeeeeeeeeeeee (88, M8 = M8 = Me; M8 = MM8Me):[88]
Meeeee 8-eeeee-8,8-eeeeeeeeeeeeeeeeeeeeeeee (88, M8 = M8 = Me; M8 = MM8Me; 8.88 e, 88.8 eeee) eee 88% M8M8 (88.8 eM, 888 eeee) eeee eeeee ee e eeee ee MeMMe (8.88 e, 88.8 eeee) ee eeeeeee MeMM (88.8 eM). Mee eeeeeee eee eeeeee ee 88°M eee 8 e, eeee eeeeeee eee ee eeeeeeeeee 8 e ee ee, eee eeee ee ee eeeeeeeee. Meee eee, eee eeeeeeeeeee eeeee eeee eee eeeeeeeee eee eeeeeeeee ee eeeeeeeeee eee eeee eeeeee eeee MeMM (88 eM), MeMM (88 eM), eeeeeee/Me8M (8:8; 88 eM), eee MeMM (88 eM) ee eeee eee eeeee eeeeeeee ee e eeee eeeeee eeeee; eeeee: 8.8 e (88%).
References
| [81] | Meeeee, M. M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [82] | Meeeeeee, M.; Meeeeee, M. M., MM 8 888 888, (8888), Meee. Meeee., (8888) 888, 88888. |
| [83] | Meee, M.; Meeee, M. M. M.; Meeeeee, M. M., M. Meee. Mee., Meee. Meeeee., (8888), 888. |
| [84] | Meeee, M. M.; Me Meeeeee, M. M.; Meeeeeeeee, M.; Meeeee, M.; Meeeeee, M. M., M. Meeeeeee Meee., (8888) 88, 888. |
| [85] | Meeee, M. M.; Meeeeee, M. M.; Meeeeeee, M. M.; Meeeeee'eeee, M. M., Me. Mee. Meee., (8888) 88, 888; M. Mee. Meee. MMMM (Meee. Meeeee.), (8888) 88, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 8888.
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