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von Angerer, S., Science of Synthesis, (2005) 26, 115.
The conversion of primary amines at a secondary carbon atom to the oxo group is a common reaction in biochemistry. Examples are the oxidative deamination of glutamate and transamination reactions which lead to the formation of α-oxocarboxylic acids. Preparative methods for the transformation of amines to ketones, e.g. 170, comprise the oxidation with potassium permanganate (Table 12, entry 1),[465,466] iodosylbenzene (Table 12, entry 3),[467] hydrogen peroxide in the presence of bromine,[468] N-(tert-butyl)benzenesulfinimidoyl chloride (Table 12, entry 5),[469] peroxydisulfate (Table 12, entry 4)[470] and 3,5-di-tert-butylbenzo-1,2-quinone (Table 12, entry 6).[471]
Meeee 88 Meeeeeeee ee Meeeeee Meeeee ee Meeeeee[888–888,888–888]
| Meeee | Meeeee 888 | Meeeeee | Meeeeeeeee | Meeee (%) | Mee |
|---|---|---|---|---|---|
| 8 | eeeeeeeeeeeee | MMeM8 | MeMM8•8M8M, M8M, e-MeMM, 888°M (eeeeeeeeeeee) | 88 | [888] |
| 8 | eeeeeeeeeeeeee | MMeM8, MeMM8•8M8M | MM8Me8, eeeeee, 88 e | 88 | [888] |
| 8 | eeeeeeeeeeeeee | MeMM | M8M, 8°M, 8 e; ee, 88 e | 88 | [888] |
| 8 | eeeeeeeeeeeee | Me8M8M8 | MeMM8, M8M, MeMM, 8–88°M, 8 e | 88–88 | [888] |
| 8 | eeeeee-8-eee | MeM(Me)=Me-Me | 8. MeMe, Me8M, MM8Me8, 8°M, 8 e8. MeM(Me)=Me-Me, MMM, MM8Me8, –88°M, 8 e8. 8 M ee MMe, MM8Me8, Me8M, | 88 | [888] |
| 8 | eeeeeeeeeeeeeee |  |
M8, MeMM, 88°M, 88 eee; MMM, M8M, eM 8, 88°M, 8 e | 88 | [888] |
Meeee eeeeeee eeeeeeeeee, eeeeeeeeeee eeeeee eee ee eeee ee eee eeeeeee. Me eeee eeee, eee eeeeeee eeeee eee ee ee eeeee eeeeeeeee eeee eee eeeeeeeeeeeeee eeeeeeeeee eeeee ee eeeeeeeee eeee eeeeeeeeeeee eee eeee eeeeeee eeee eee.[888] Meeee eeee eeee eeee eeeeeeee ee eeeee eee eeeeeeeeeee eeeeeeeeeeeeee ee eeeeee ee eeeeeee ee eeeee eeeeeeeeeeeeee[888] ee eeeeeeeeeeeee-8-eeeeeeeeeeee[888] eee eee eeeeeeeee ee ee eeeeeeeeeeee Meeeee eeee. Mee eeeee 888 eeeeeeee eeee eee eeeee 888 eeee eeeeeeeeeeeeee (888) eeeeeeeeeeee eeee eeeeeeeee eeee eeee ee eeee eeeeee 888 (Meeeee 888). Meeeeeeeee eeeeeeeeee ee 888 eeeee eee eeee eeeeee 888 ee 88% eeeeeee eeeee.[888]
Meeeee 888 Meeeeeeeee ee Meeeeeeeeeeeeeeee eeee Meeeeeeeeeeeeee eee ee Meeee Meeeeeeeeeee eee Meeeeeeeeeeeee Meeee Meeeeeee[888]
Meeeeeeeeeee Meeeeeeee
Meeeeeeeeeeeeee (888); Meeeeee Meeeeeeee:[888]
Me e eeee ee eeeeeeeeeeeeeeeee (888; 888.8 ee, 8.8 eeee) ee eeeeeee (8 eM) (MMMMMMM: eeeeeeeeee) eee eeeee e eeee ee eeeeeeeeeeeeee (888; 888 ee, 8.8 eeee) ee eeeeeee (8 eM) ee 88°M, eee eeeeeeee eee eeeeeeeee eee 88 eee eeeee M8. Meeee eeeeeee ee eee eeeeeee, eee eeeeeeeee Meeeee eeee 888 eee eeeeeeeee ee e eeee ee MMM (8.8 eeee) ee MMMM/MMM (8:8, 8 eM). Mee eeeeeeee eee eeeeeee ee eeeeeee eee 88.8 e eeeee M8, eee eeee eee eeeeeee eee eeeeeeeee ee eeeeeeeeee ee eM 8 eee 8 e eeee eeeeeeee ee 88°M eeeee eeeeeeee ee MeMM/MMM (8:8, 8 eM) eee eeeeeeeeeee eeeeee eeee eeeeeeeee. Meeeeee eeeeeeeee eee eeeeeeeeeeee ee eeeeeee eeeeeeeeeeeee, eeeeeeee ee eeee-ee-eeee eeeeeeeeeeee ee 888°M (eeee eeeeeeeeeee)/8 Meee; eeeee: 88%; ee 88–88°M.
References
| [465] | Meeeeee, M. M.; Meeeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [466] | Meeeeeeee, M. M.; Meeeeeeeee, M. M., Meeeeeeee, (8888), 888. |
| [467] | Meeeeeee, M. M.; Meee, M. M.; Meeeee, M. M.; Meeeee, M.; Meeeeee, M.; Meeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [468] | Meeeeeee, M. M.; Meeeeee, M.; Meeeeee, M.; Meeeeee, M., Meee. Meeeee. (Meeeeeeee), (8888), 888. |
| [469] | Meeeee, M.-e.; Meeeee, M.; Meeeee, M.; Meeeeeeee, M., Meee. Meee., (8888), 888. |
| [470] | Meeee, M. M. M.; Meeee, M. M. M.; Meeeeee, M., M. Meee. Mee. M, (8888), 8888. |
| [471] | Meeee, M. M.; Meeeee, M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [472] | Meee, M. M.; Meeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [473] | Meee, M.; Meeee, M.; Meeeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8e, 888.
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