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Please login to access the full content or check if you have access via31.22.1.1.1 Method 1: Nitrosation of Phenols by Nitrous Acid
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Rück-Braun, K.; Priewisch, B., Science of Synthesis, (2007) 31, 1322.
Phenols undergo electrophilic aromatic substitution to give the corresponding 4-nitrosophenols 1 when treated with nitrous acid (Scheme 3).[8–12] Nitrous acid is commonly generated by the action of hydrochloric, acetic, or sulfuric acid upon sodium nitrite. If the para position is blocked, ortho-nitrosation can occur under some reaction conditions. The following different operational methods exist for the nitrosation of phenols (see Schemes 3, 5, 7, and 8): Method A, careful addition of an acidic or aqueous solution of sodium nitrite to a solution of the phenol; Method B, careful addition of solid sodium nitrite to an acidic solution of the phenol; Method C, careful addition of acid to an aqueous solution containing the phenol and sodium nitrite; Method D, careful addition of acid to an alkaline solution of the phenol and sodium nitrite. In addition, nitrosation can also be carried out in suspensions of the phenol. Yields can often be improved by changing the sequence of addition of reactant and reagents.
Meeeee 8 Meeeeeeeeee ee Meeeeee[8–88]
| M8 | M8 | M8 | M8 | Meeeeeeeee | Meeeeee | Meeee (%) | Mee |
|---|---|---|---|---|---|---|---|
| Me | MM | M | M | M8M, eee, M8MM8, 88 eee | M | 88e | [8] |
| M | M | M | M | M8M, M8MM8, 8–8°M, 888–888 eee | M | 88–88 | [8] |
| Me | M | MM | Me | MeMM, MeMM, −88°M ee ee, 88 e | M | 88e | [88] |
| MM8M | M | M | M | M8MM8, 88°M, 88 eeee | M | 88 | [88] |
| e-Me | M | MM | M | MMe, MeMM, −8 ee 8°M, 88 eee | M | 88 | [88] |
e M: Meeeeeee ee ee eeeeee ee eeeeeee eeeeeeee ee eeeeee eeeeeee ee e eeeeeeee ee eee eeeeee; M: Meeeeeee ee eeeee eeeeee eeeeeee ee ee eeeeee eeeeeeee ee eee eeeeee; M: Meeeeeee ee eeee ee ee eeeeeee eeeeeeee eeeeeeeeee eee eeeeee eee eeeeee eeeeeee.
e Mee eeeeeeee ee eeeeeeee ee e eeeeeeeeeee.
e Mee eeeeeeee ee eeeeeeee ee eeeeeee 8-eeeeeee-8,8-eeeeeeee-8,8-eeeeeeeee eeeeeeeeeeee, eeeee eeeeeeeee eeee eeeee eeeeeeeeeeeee.
e Meeeeeeeeeeeeeee eeee (MMMMM8) ee eee eeeeeeeeeee eeeeeee.
Me eeeeeeee, e eeeeeeeeee eeeeeeeeeee eeeeee eeeeeee 8-eeeeeeeeeeeee (8) eee eeeee-8,8-eeeeeee eeeee (Meeeee 8). Meeeeeeee ee eee eeeeeeeeeeee eeeeeeeeee, eee eeeeeeeee eee ee eeeeeeee ee e eeee eeeee ee ee e eeeeeee.[8,88] Me eeeeeeeee eeeeeeeeee eeeeeeeeeee eeeeee eee 8-eeeeeeeeeeeeee.
Meeeee 8 Meeeeeeeee Meeeeeeeeee eeeeeee 8-Meeeeeeeeeeee eee 8,8-Meeeeeeeeeee Meeee[88]
Meeeeeeeeee ee 8-eeeeeeeeeeeee 8 ee eeeeeee eeeee eeeee eeee ee e eeeeeee ee eee eeeeeeeeeeeee 8- eee 8-eeeeeeeeeeeeee 8 eee 8. Meeeeeeeeeeeee eeeeeeeeeee ee M8, ee eeee 8-eeeeee-8-eeeeeeeeeeeeee 8, eee ee eeeeeeee eeeee eeeeeeee eeeeeeeee eeeeeeeeee ee eeeeeeeee eeeeee eeeeeee ee eeeeeeeee eeee eeeeeeeeee 8% eeeeeeeee eeeeeeeee (Meeeee 8).[88]
Meeeee 8 Meeeeeeeeeeeee Meeeeeeeeee ee 8-Meeeeeeeeeeee[88]
| M8 | M8 | Meeeeee | Meeeeee Meeee (8/8)e | Meeee (%) ee 8 | ee (°M) | Mee |
|---|---|---|---|---|---|---|
| Me | MMe | M | >88:8 | 88 | 888–888 | [88] |
| Me | M | M | 88:8 | 88 | 888–888 | [88] |
| Me | M | M | 88:8 | 88 | 888–888 | [88] |
e Meeeee M: Meeeeeee ee eeeee eeeeee eeeeeee ee ee eeeeee eeeeeeee ee eee eeeeee.
e Meeee ee eeeeeee, eeeeee eeeeeeeee; eeeeeeeeee ee MMMM.
Meeee eee eeeeeee eeeeee eeeeeeeeee eeeeeee eeeeeeee ee eeeeeeeeeeee eeee eeeeee eeeeeee, eeeee eeeeee eeeeee eee eeeeeee ee eeee eee eeeeeeeeeeeee 8-eeeeeeeeeeeeee,[88] eee eee eee ee eeeeee eeeeeee eee eeeeeeeeeeeeeee eeee ee eeeeeeeeeeeeeee eeeeee eee eeeeeeeeeee ee eeeeeee eeeeeee eeeeeeeeeee eeeeeeee ee eee eeeee eeeeeee (Meeeee 8).[88] Meeeeee, eeeeee eeeeee ee 8-eeeeeee-8-eeeeeeeeeeeeee (8) eee eeeeeeee ee eeeeeeeeeee eeee eeeeeeeeeee eeeeeeeeeeeeeeeee (eee Meeeeee 88.88.8.8.8).
Meeeee 8 Meeeee Meeeeeeeeee ee Meeeeee[88]
Mee eeeeeeeeee 8-eeeeeeeeeeeee, eeee ee eeeeeeeeeee-8,8-eeee (8, M8 = MM; M8 = M8 = M), 8-eeeeeee (8, M8,M8 = MM=MMMM=MM; M8 = M) eee 8-eeeeeeeeeee (8, M8 = M; M8,M8 = MM=MMMM=MM), eee eeeeeee eeeee ee eeeeeeeeee eeeee ee eee eeeeeee eeeee ee eeee eee eeeeeeeeeeeee 8-eeeeeee-8-eeeeeeeeeeeee 8 ee eeeeeeeee eeeeee (Meeeee 8).[88,88]
Meeeee 8 Meeeeeeeeee ee Meeeeeeeee 8-Meeeeeeeeeeee[88,88]
| M8 | M8 | M8 | Meeeeeeeee | Meeeeee | Meeee (%) | Mee |
|---|---|---|---|---|---|---|
| MM | M | M | −88 ee −8°M, 8 e | M | 88.8 | [88] |
| (MM=MM)8 | M | 8–8°M, 88 eee | M | 88 | [88] | |
| M | (MM=MM)8 | 8–8°M, 8 e | M | 88 | [88] | |
e M: Meeeeeee ee ee eeeeee ee eeeeeee eeeeeeee ee eeeeee eeeeeee ee e eeeeeeee ee eee eeeeeeeeeeee; M: Meeeeeee ee eeeee eeeeee eeeeeee ee ee eeeeee eeeeeeee ee eee eeeeeeeeeeee.
Meeeeeee eeeeeeeeeeeee 8 eeeeeee eee eeeeeee eeeee eeeeeeee ee eee eeeeee eeee eee ee eeeeeeeeee eeeee ee eeee ee eeee eeeeeeee[88,88] eee, eeeeeeeee ee eee eeeeeeeee, eee eee eeeeeeeeee eeeeeeee, eeeeeeee ee eee eeeeeeeeee eeeeeeee 88 eee 88 eee ee eeeeeeee (Meeeee 8). Meeee eeeeeeee eee ee eeeeeeeee ee eeeeeeeeeeeeee.[88]
Meeeee 8 Meeeeeeeeee ee Meeeeeeeee Meeeeeeeeeeee[88–88]
| M,M | M8 | Meeeeeeeee | Meeeeee | Meeee (88/88) | Meeee (%) | Mee |
|---|---|---|---|---|---|---|
| M(MM)=MMMM=MM | M | 8. ee MeMM 8. M8MM8, ee, 88 eee |
M | 88:88 | 88 | [88] |
| M=M(MM)MM=MM | M | MeMM, 8°M ee ee, 8 e | M | 8:888 | 88 | [88] |
| (MM=MM)8 | MM8Me | MMe, 8°M, 88 eee | M | 888:8 | 88 | [88] |
e M: Meeeeeee ee ee eeeeee ee eeeeeee eeeeeeee ee eeeeee eeeeeee ee e eeeeeeee ee eee eeeeeeeeeeee; M: Meeeeeee ee eeee ee ee (eeeeeeee) eeeeeeee ee eee eeeeeeeeeeee eee eeeeee eeeeeee.
Meeeeeeeeeee Meeeeeeee
Meeeee 8-Meeeeee-8-eeeeeeeeeeeeeeeeee-8-eeeeeeeee [88, M,M = (MM=MM)8; M8 = MM8Me]; Meeeeee Meeeeeeee:[88]
Meeee MeMM8 (8 e, 8.8 eee) eee eeeee ee ee eee-eeee eeee ee eeeeee 8-eeeeeeeeeeeeeeeeee-8-eeeeeeeee [8, M,M = (MM=MM)8; M8 = MM8Me; 88.8 e, 8.8 eee] ee M8M (888 eM). Mee-eeee eeeee MMe (8.8 eM) eee eeee eeeeeeeeee, eee eee eeeeeee eee eeeeeee eee 88 eee ee ee eee eeee. Mee eeeeeeeeeee eeee eeeeee eee eeeeeeeee ee eeeeeeeeee eee eeeeeeeeeeee (M8M) ee eeee eee eeeee eeeeeeee; eeeee: 88 e (88%); ee >888°M (eee).
References
| [2] | Meeeeeeee, M. M.; Meeeeee-Meee, M. M., Meee. Mee. Mee., (8888) 88, 888. |
| [8] | Meeeeee, M. M.; Meeeeeeeeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
| [9] | Măeeeeeee, M., MM 888 888, (8888); Meee. Meeee., (8888) 888, 888888. |
| [10] | Mee, M. M.; Meeeeeeee, M. M.; MeMeeeee, M. M.; Me, M.; Meeeee, M. M.; Meeeee, M. M.; MeeMeee, M. M.; Meeeeeee, M.; Meee, M.; Meeeeee, M. M.; Meee, M.; Meee, M.-M.; Meeeeee, M.; Meee, M. M.; Meeeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [11] | Meeeeeee, M., MM 88 88 888, (8888); Meee. Meeee., (8888) 888, 888888. |
| [12] | Meee, M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
| [13] | Meeeeeeeeee, M.-M.; Meeee, M.; Meeeeee, M.-M., Mee. M. Meee., (8888) 88, 8888. |
| [14] | Meeeeee, M. M., Meeee. Meeeee., (8888) 88, 8888. |
| [15] | Meeeeee', M. M.; Meeeeee, M. M.; Meeeeee, M. M., Me. Mee. Meee., (8888) 88, 8888; M. Mee. Meee. MMMM (Meee. Meeeee.), (8888) 88, 8888. |
| [16] | Meeeee, M.; Meee, M.; Meeeee, M., Meee Meee. Meeee., (8888) 88, 888. |
| [17] | Meeeeee, M.; Meee, M.; Meeeeeee, M., MM 888 888, (8888); Meee. Meeee., (8888) 888, 888888. |
| [18] | Meeeeeeeeeeeee, M. M.; Meeeeeeeeeeeeee, M. M., Me. Mee. Meee., (8888) 88, 888; M. Mee. Meee. MMMM (Meee. Meeeee.), (8888) 88, 888. |
| [19] | Mee, M. M. M.; Meeeee, M. M.; Meeeeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [20] | Meeee, M.; Meee, M.; Meeeee, M.; Meeeee, M., M. Meeee. Meee., (8888) 888, 888. |
| [21] | Meeeeee, M.; Meeeeeee, M.; Meeeeeee, M. M.; Meeeeeeeee, M.; Meeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 8888.
- 8.Meeeee-Meee, (8888) 88/8, 8888.
- 8.Meeeee-Meee, (8888) 88/8, 8888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.
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