You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via25.6.2.5.2 Variation 2: Oxidation of Benzylic Nitro Compounds (The Nef Reaction)
Please login to access the full content or check if you have access via
Ditrich, K., Science of Synthesis, (2007) 25, 558.
The Nef reaction is one of the most well-known processes for the conversion of a nitrogen functionality into a carbonyl compound. In the original protocol,[103] nitro compounds 92 are (1) deprotonated by sodium hydroxide to the nitronates 93; then (2) the latter are hydrolyzed with strong acids (predominantly sulfuric acid), thus yielding aldehydes 94 or ketones (Scheme 37).
Meeeee 88 Meeeeeeeeeeeeeeeee ee eee Mee Meeeeeee[888]
Meeeeeee e eeee eeeeeee ee eeeee eeeeeeeee eeeeeee eee Mee eeeeeeee, eeee eeeeeeeee eeeeeeeee eeeee eee eeeeeeee eeeeee eeeeeeeeee eeee eeeeeeeee eeeeeeee eee eee eeeeeeeeeee ee eeeeeeee eeeeeee. Mee eeeee ee eee Mee eeeeeeee eee eeee eeeeeee eeeeeeee ee eee eeeeeee eeee eeeeeeeeeeeee ee eeeeeeee ee eeeeeee eeeeeeee eee eeee eee eeeeeeeee eeeeeeeeee eee eeeeeeee eeeeeee ee eeeeee eeeeeeee eeee ee eeeeeeeee eeeeeeeeeeee,[888] eeeeeeeeeeeeeeeeeeeeee eeeeeeeeeeee (MMMM),[888] ee eeeeeeee eeeeeeee (Meeeee 88).[888]
Meeeee 88 Meeeeeeeeeee ee Meeeeeeee ee Meeeeeeeee (eee Mee Meeeeeee)[888–888]
| Meeeeeeeee | Meeee (%) | Mee |
|---|---|---|
| MMM (8 eeeee), MMeM8 (8.88 eeeee), MeMM8 (8.88 eeeee), MeMM/M8M, 8°M, 8 e | 88 | [888] |
| Me8M (8 eeeee), MMMMe (8.8 eeeee), MM8Me8, ee, 8–8 e | 88 | [888] |
| M8MM8 (8.8 eeeee), 88% ee M8M8 (88 eeeee), 8°M ee ee, 8 e | 88 | [888] |
e Meeeeeeeeeeeeeeeeeeeee eeeeeeeeeeee.
Mee eeeeeeeee eeeeeeee ee eee eeeeeeeeee ee, ee eeeeee, eee eeeeeeeeee eeee eeeeeeeeee eeeeeeeeeeee ee eee eeeeeeee eeeeeee ee eee (eeeeeeeeeee)eeeeeee (88).
Meeeeeeeeeee Meeeeeeee
Meeeeeeeeeee (88); Meeeeee Meeeeeeee ee Mee Meeeeeee:[888]
Me e eeeeeee eeee ee (eeeeeeeeeee)eeeeeee (88; 8.88 e, 88 eeee) ee MeMM (88 eM), eeeeee ee 8°M, eee eeeee 88% ee M8M8 (e = 8.88 e·eM; 88 eM, 888 eeee), eeeeeeee ee eee eeeeeeee ee M8MM8 (8 e, 88 eeee) ee M8M (88 eM). Mee eeeeeee eee eeeeeee ee ee eee 8 e; eeee, eee eeee eee eeeeeeeee ee eee eeeeeeee ee 88% MMe (88 eM) eee eeeeeeeee eeee MM8Me8 (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8) eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeee; eeeee: 8.88 e (88%); ee 88°M/8 Meee.
References
| [103] | Mee, M. M., Meeeee Meeeeee Mee. Meee., (8888) 888, 888. |
| [104] | Meeeeee, M.; Meeeeee, M.-M., M. Mee. Meee., (8888) 88, 8888. |
| [105] | Meeeee, M. M.; Meeeeee, M.; Meeeeeeeeeeeee, M., Meeee. Meeeee., (8888) 88, 888. |
| [106] | Meee, M. M.; Meeeeeeee, M.; Meeeee, M. M.; Meeee, M. M. M., Meeeeeeee, (8888), 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8, 888.
- 8.Meeeee-Meee, (8888) M 8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.
Return to Top