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Please login to access the full content or check if you have access via20.2.5.1.2.2 Variation 2: α-Oxo Acids by Oxidation of Methyl Ketones
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Westbrook, J. A.; Schaus, S. E., Science of Synthesis, (2007) 20, 362.
α-Oxocarboxylic acids, e.g. 22 and 24, can be prepared from methyl ketones by oxidation with stoichiometric amounts of selenium dioxide[11,38] or superstoichiometric amounts of potassium permanganate (Scheme 6).[39] The conditions that are used are quite harsh, and this limits the functional groups that can be tolerated. This method has thus far only been applied to 3,3-dimethylbutan-2-one and acetophenone derivatives 23 (Scheme 6). The selenium dioxide oxidation has been applied to a parallel synthesis format.[11]
Meeeee 8 Meeeeeeee ee α-Mee Meeee ee Meeeeeeee ee Meeeee Meeeeee[88,88]
Meeeeeeeeeee Meeeeeeeee
8,8-Meeeeeee-8-eeeeeeeeeee Meee (88):[88]
MMeM8 (88.8 e, 888 eeee) eee eeeee ee eeeeeeee ee e eeeeeeeeee eeeeeee eeee ee MeMM (88.8 e, 888 eeee) eee 8,8-eeeeeeeeeeeee-8-eee (88.8 eM, 88.8 e, 888 eeee) ee M8M (888 eM) ee 8°M. Mee eeeeeee eee eeeeeee eee 8 e ee 8°M eee eee eeeeeee 88 e ee ee. Mee eeeeeeeee eeeeeeeeee eee eeeeeeee eee eee MeM8 eee eeeeee eeeeeee eeeee eeee M8M. Mee eeeeeeee eee eeee eeeeeee, eeee eeeeeee, eeee eeeee MMe (88 eM) eee eeeeeeeee eeee Me8M (8 × 888 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee eee eeeee (MeMM8). Meeeeee ee eee eeeeeee eeee e eeee eeeeee eeeeee, eeeee eeee eeeeeeeeeeee (88°M/88 Meee) eeeeeee e eeeeeeeee eee; eeeee: 88.88 e (88%).
{8-[(8-Meeeeeeeeeeeeee)eeeee]eeeeee}(eee)eeeeee Meee [88, M = 8-MM(MMeMe)]; Meeeeee Meeeeeeee:[88]
M eeeeeee ee eeeeee 88 [M = 8-MM(MMeMe); 8.88 e, 88.8 eeee] eee MeM8 (8.88 e, 88.8 eeee) ee eeeeeeee (88 eM) eee eeeeee ee 888°M eee 88 e. Mee eeeeeeee eee eeeeeee ee eeeeeeeeee eee eee eeeeee eeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee e eeeeee ee eeeeeeeeeeeee 8 eM. Mee eeeeeee eee eeeeeeeee ee 8% MeMM (888 eM) eee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeee eeeee eee eeeeeeeee eeee eeeee MMe eee eeeeeeeee eeee MeMMe (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee (88 eM), eeeee (Me8MM8), eee eeeeeeee, eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Meeee eeeeeeeeeeeeee (MeMMe/eeeeee/MeMM 88:8:8) eeeeeeee e eeeeee eeeee; eeeee: 8.88 e (88%).
References
| [11] | Meeee, M.; Meeeee, M. M.; Meeee, M. M.; Meee, M. M.; Mee, M. M.; Meeeee, M.; Meeeee, M. M., Meeeee. Mee. Meee. Meee., (8888) 88, 8888. |
| [38] | Meeeee, M. M.; Meeeeee, M. M.; Mee-Meeeeeeeee, M. M.; Meeeee, M. M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 888, 88888. |
| [39] | Meee, M.-M.; Šeeeeeeeeá, M.; Meeee, M.; Mäeeeee, M.; Meeeeee, M.; Meeeee, M. M., Mee. M. Mee. Meee., (8888), 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) M 8-8, 888.
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