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Aitken, K. M.; Aitken, R. A., Science of Synthesis, (2007) 31, 1186.
Fuming nitric acid can be used in the nitration of aromatic compounds with one or more deactivating substituents, including cases where multiple nitrations of an aromatic ring are attempted. In this section the use of over 70% HNO3 (d >1.4 g·mL−1) is considered. In some references, red fuming nitric acid, which is 100% nitric acid prepared from potassium nitrate and concentrated sulfuric acid, is used.[22]
Me 8888, eeeeeeee (8M-8-eeeeeeeeee-8-eee, 8) eee eee eeeee eeeeeeee ee ee eeeeeeee eeeeeeeeeeee eeee eeeeee eeeeee eeee, ee eeee 8-eeeeeeeeeeeee (8) (Meeeee 8).[88,88] Mee eeeeeeeeee eeeeeeeeee ee 8,8,8-eeeeeeeeeeeeeee (8) ee eeeeeeeee ee eee eeeee eeeeee ee eeeeeee eee eeeeeeee eeeeee eeeeeeeeee eee eeeeeeeee, eeeee eee ee eeeeeeeee ee eee eeeee eeeeeeee eeee eeeeeee (8) eeeee eeeeee eeeeee eeee.[88,88] Meeee 8 eeeee eeeeeeee ee eeee-, ee-, eee eeeeeeeeeeeee eeeee eeeeee eeeeee eeee ee eeeeeee eeeeeeeeeeeeee.[88,88–88]
Meeeee 8 Meeeeeeee ee Meeeeeee eee Meeeeeeeeeee ee Meeeeee Meeee Meeeee Meeeee Meee[88–88]
Meeee 8 Meeeeeeee Meeee Meeeee Meeeee Meee[88,88–88]
| Meeeeeee | Meeeee Meee Meeeeeeeeeeee (%) | Meeeeeeeee | Meeeeee(e) | Meeeee (%) | Mee |
|---|---|---|---|---|---|
| eeeeeeeeeeeee | 88 (8 eeeee) | 88–88°M | 8,8-eeeeeeeeeeeeee | e.e. | [88] |
| eeeeeeeeeeee | 888 | 8°M, 8 e | 8-eeeeeeeeeeeeeeeee+ 8-eeeeeeeeeeeeeeeee+ 8-eeeeeeeeeeeeeeeee |
88+88+8 | [88] |
| eeeeeeee | 88 (ee Me8M) | ee, 88 e | 8-eeeeeeeeeeeee | 88 | [88] |
| eeeeee 8,8-eeeeeeeeeeeeeeeee | 88 | 88–88°M, 88 eee | eeeeee 8,8-eeeeeeeee-8,8-eeeeeeeeeeeeeee | 88 | [88] |
| 8′-eeeeeeeeeeeeeeeee | 88 | −88°M, 8 e | 8′-eeeeee-8′-eeeeeeeeeeeeeeee+8′-eeeeee-8′-eeeeeeeeeeeeeeee | 88+88 | [88] |
| 8,8-eeeeeeee-8-eeeeeeeeeeeeee eeee | 88 (ee MeMM8) | 88°M, 8 e | 8,8-eeeeeeee-8-eeeeeee-8-eeeeeeeeeeee eeee | 88 | [88] |
| eeeeeeeeeeeeeeeeee | eeeeee | eeeeee eeee, eee eee | eeeeeeeeeeeeeeeeeeeeeee | e.e. | [88] |
| 8-eeeeeee-8-eeeeeeeeeeeeeeeeeee | eee eeeeee | 8–88°M, 8.8 e | 8-eeeeeee-8-eeeeeee-8-eeeeeeeeeeeeeeeee | 88 | [88] |
e e.e. = eee eeeeeeee.
e Meeeeeeeeee eeeeee eeeeeee.
Mee eeeeeeeeee ee 8,8-eeeeeeeee-8-eeeeeeeeeeee (8) eeee 8,8-eeeeeeeee-8,8-eeeeeeeeeeeeee (8) eeeee eeeeee eeeeee eeee eeeeeeeeeee eee eeeeeeeee ee eeeeeeeeeee eeeeeeee eeeeeeeee (Meeeee 8).[88] Mee eeeeeeee ee 8-eeeeeeeee (88) eeeee e eeeeeee ee eeeeeee 88 eee 88 eeee eee ee eeeeeeeee ee eeeeee eeeeeeeeeeeeee.[88] Me eee eeeeeeeee ee 8,8-eeeeeeeee-8-eeeeee-8-eeeeeeeeeeeeee (88) eeee 8,8-eeeeeeeee-8-eeeeeeeeeeeeeee (88), eee eeeeeeee eeeeeee eeeeeeeeeeeee ee eee eeeeeee eee eeee eeeee eeee eeeeeee eeeeee eee eeeeeeee eee eeeeee.[88]
Meeeee 8 Meeeeeeee Meeee Meeeee Meeeee Meee[88–88]
Meeeeeeeeeee Meeeeeeee
8,8-Meeeeeeee-8,8-eeeeeeeeeeeeee (8):[88]
8,8-Meeeeeeee-8-eeeeeeeeeeee (888 e, 8.88 eee) eee eeeee eeeeee eeee eeeeeee ee MMM8 (e 8.88 e·eM−8; 8888 eM, 88.8 eee), eeeeeee eee eeeeeeeeeee ee eee eeeeeee eeeee 8°M. Meeee eee eeeeeeee eee eeeeeeee, eee eeeeeee eee eeeeee eeee M8M (8 M) eee eee eeeeeeeeeee eee eeeeeeeee ee eeeeeeeeee eee eeeeee eeee M8M. Mee eeeee eeeeeee eee eeeeeeeeeeeeee (MeMM) ee eeee eee eeeeeee ee e eeeeeeeeeee eeeee; eeeee: 888 e (88%); ee 888–888°M.
8-Meeee-8-eeeeeeeee (88) eee 8-Meeee-8-eeeeeeeee (88):[88]
Meee (−88°M) 88% MMM8 (8 eM, 888 eeee) eee eeeeeee eeeeeeeeee eeeee 8-eeeeeeeee (88; 888 ee, 8.8 eeee) eee eeeeee eeeee. Meeee eee eeeeeeee eee eeeeeeee, eee eeeeeee eee eeeeeee eee 8 eee, eeeeee eeee e eeeeeee ee MeMM (8.8 e) ee M8M eee eee (ee. 88 eM), eee eeee eeeeeeeee eeee MeMMe (8 ×). Mee eeeeeeee eeeeeeee eeee eeeeee eeee M8M eeeee eeeeeee eee eeee eeeee (MeMM8). Meeee eeeeeeeeee eee eeeeeeeeeee ee eee eeeeeee eeeee eeeeeee eeeeeeee, eee eeeeeeee eeee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 8:8). Mee eeeee eeeeeeee eeeeee eee 8-eeeee-8-eeeeeeeee (88), eeeee eee eeeeeeeeeeeeee (MeMMe); eeeee: 888 ee (88%); ee 88–88°M; MMM (eeeeee/MeMMe 8:8) Me 8.88; 8-eeeee-8-eeeeeeeee (88) eeeeee ee eee eeeeee eeeee eeeeeee eee eee eeeeeeeeeeeeee (MeMMe/eeeeee); eeeee: 888 ee (88%); ee 88–88°M; MMM (eeeeee/MeMMe 8:8) Me 8.88.
8,8-Meeeeeeee-8-eeeeee-8-eeeeeeeeeeeeee (88):[88]
8,8-Meeeeeeee-8-eeeeeeeeeeeeeee (88; 8.8 e, 88.8 eeee) eee eeeee, eeeeeeeeeee eeee 8 e, ee eeeeee MMM8 (88 eM, 8.88 eee), eeeeee ee −88°M eeeee eeeee, eeeeeeee eeee eee eeeeeeeeeee eee eee eeee eeeee −88°M. Mee eeeeeee eee eeee ee eeee eee 88 eee, eeee eee eeeeeeeeeee eeee eeeee −88°M. Me eee eeee eeeeee eeee eee eee eee eeeeeeeeeee eee eeeeeeeeee eeeeeee −88 eee 8°M eeeee eee eeee eee eeeeeeeeeee eeee 88% ee MeMM (888 eM). Mee eeeeeee eee eeee eeeeeeeeee eeeeeeeee eeee MM8Me8. Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee 88% ee M8MM8, eeeee, eee eeeeeeeeeeee ee eeee e eeeee eeeee; eeeee: 8.88 e (88%); ee 888°M.
References
| [17] | Meeeee, M. ee M., MM 8 888 888, (8888); Meee. Meeee., (8888) 88, 88888. |
| [22] | Meeee, M. M.; Meeeeee Meeeeeeeee, M., Mee. M. Meee., (8888) 88, 888. |
| [23] | Meeeeeeee, M., Mee. Meee. Meee., (8888) 8, 888. |
| [24] | Meeeeeeee, M., Meeeee Meeeeee Mee. Meee., (8888) 88, 888. |
| [25] | Meeeeeee, M. M., MM 8 888 888, (8888); Meee. Meeee., (8888) 88, 88888. |
| [26] | Meeeeeee, M. M., MM 8 888 888, (8888); Meee. Meeee., (8888) 88, 88888. |
| [27] | Meeeee, M. M.; Mee Meeee, M., Meee. Meee. Meee. Meee-Mee, (8888) 88, 888. |
| [28] | Meeeeeeee, M., Meee. Meee. Meee. Meee-Mee Meee., (8888) 88, 88. |
| [29] | Meeeeeeeeee, M.; Meeeeee, M., Meeeeee. Meee., (8888) 88, 888. |
| [30] | Me Meeee, M., Meee. Meee. Meee. Meee-Mee Meee., (8888) 88, 888. |
| [31] | Meeeeeeeee, M.; Meeeeeee, M.; Meöee, M.; Meeeeeeeee, M.; Möeeeee, M.; Meeeeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeeeeeee, M., Mee. M. Mee. Meee., (8888) 88, 888. |
| [32] | Meeeeeeeeee, M., Mee. Meee. Meee., (8888) 88, 888. |
| [33] | Meeeee, M. M.; Meeeeeee, M., M. Meeee. Meee., (8888) 888, 888. |
| [34] | Meeeeee, M.; Meeeeee, M., Meee. Meee. Meee, (8888) 88, 888. |
| [35] | Meee, M. M.; Meeeeeeee, M. M.; Meeeee, M.; Mee, M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 88888. |
| [36] | Meeeeee, M.; Meeee, M. M.; Meee, M. M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) M 88-8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.
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