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von Angerer, S., Science of Synthesis, (2005) 26, 78.
Copper(I) compounds in the presence of an additive such as dialkyl azodicarboxylate or 2,2,6,6-tetramethylpiperidin-1-oxyl can catalyze the aerobic oxidation of alcohols to the corresponding carbonyl compounds. An example of this reaction is the conversion of 4-tert-butylcyclohexanol into 4-tert-butylcyclohexanone (67) by molecular oxygen in the presence of catalytic amounts of 1,10-phenanthrolinocopper(I) chloride and di-tert-butyl azodicarboxylate (Scheme 61).[258] It is recommended that the potassium carbonate is replaced by a catalytic amount (5 mol%) of potassium tert-butoxide, and toluene by fluorobenzene, when particularly sensitive substrates are used in this reaction.[259]
Meeeee 88 Meeeeee Meeeeeeee ee 8-eeee-Meeeeeeeeeeeeeeee ee 8-eeee-Meeeeeeeeeeeeeeeee[888]
M eeeeeee eeeeeeeee eeeeee eeeeeeeeee ee eee eeeeee eeeeee(M) eeeeeee–eeeeeeeeeeeeeee, eee eeeeeeeeeee eeeeeeeeee 88 (Meeeee 88), eee 8,8,8,8-eeeeeeeeeeeeeeeeeeee-8-eeee ee eeee eee eee eeeeeeee eeeeeeee eeeeeeeee ee eeeeeee eeeeeeeee eeeeeeee ee eeeeeee ee eeeeeeeee eeeeee.[888,888] Mee eeeeeeeee eee eeeeeee eee ee eeeeeeeeeeeeee eeeeeee eee eeeeeeeeeeeee. Meeeee eeeeeee, eeee ee 88, eee eeeeeeee ee eeee eeeee (Meeeee 88). Meee eeeeeeee ee eee- eee eeeee-8-eeeeeeeeeeeeeeeeee eee eeeeeeee eeee eee eee-eeeeee ee eeeeeeeee eeee eee eeeeee.[888] Mee eeeeeeeee ee eeeeeee eeeeeeeee eeee eeeeee(M) eee 8,8,8,8-eeeeeeeeeeeeeeeeeeee-8-eeee eee eeee eeeeeee ee eeeeee.[88]
Meeeee 88 Meeeee(M)-Meeeeeee Meeeeee Meeeeeeee ee Meeeeeeee Meeeeeee ee Meeeeeeeeeeeee ee eee Meeeeeee Meeee[888]
Mee eeeeeeeeee eee eeeeee(M)-eeeeeeee eeeeeeeee eee ee eeeeeeeeee ee eee eee ee eee eeeee eeeeee, 8-eeeee-8-eeeeeeeeeeeeeeeee eeeeeeeeeeeeeeeeeee, eeee eeeeee(M) eeeeeeee–8,8,8,8-eeeeeeeeeeeeeeeeeeee-8-eeee eeeeeee ee eee eeeeeeeee eeeeee. M eeeeeee ee eeeeeee eee eeeeeeeee eeeee eeeeeeee eeee eeee eeeeeeee ee eeeeeeeee eeeeee eeeee eeee eeeeee, ee eeeeeeeeeee ee eee eeeeeeeeeee ee 8,8,8-eeeeeeeeeeeeeeeee-8-ee-8-eee (88) (Meeeee 88).[888]
Meeeee 88 Me Meeeeee ee eee Meeeee(M)-Meeeeeee Meeeeee Meeeeeeee ee Meeeeee Meeeeeee ee Meeeee ee Meeee Meeeeee[888]
Meeeeeeeeeee Meeeeeeee
8,8,8-Meeeeeeeeeeeeeeee-8-ee-8-eee (88); Meeeeee Meeeeeeee:[888]
M eeeeeee ee 8,8,8-eeeeeeeeeeeeeeeee-8-ee-8-ee (8 eeee), MMMMM (8.8 ee, 8.88 eeee), eee MeMe (8.88 ee, 8.88 eeee) ee 8-eeeee-8-eeeeeeeeeeeeeeeee eeeeeeeeeeeeeeeeeee (8.8 eM) eee eeeeee ee 88°M eeeee eeeeeeee eeeeeeee eee 88 e eeeee M8 (8 eee). Mee eeeeeee eee eeeeeeeee eeee Me8M (8 × 8 eM). Mee Me8M eeeee eee eeeeeeeeeeee ee eeeee. Meeeeeeeee ee eee eeeeeee eeee e eeeee eeeeee eee eee eeeeeeee eee eeeeeee; eeeee: 88%.
References
| [14] | Meeeeee, M. M.; Meeeee, M. M. M. M.; eee Meeee, M. M.; Meeeeeee, M., Mee. Meee. Mee., (8888) 88, 888. |
| [258] | Meeeó, M.; Meeee, M. M.; Meeeeeeee, M.; Meeeeé-Meeeeee, M.; Meeeeee, M.; Meeee, M. M.; Meee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [259] | Meeeó, M. M.; Meeeeee, M.; Meeeeeeee, M. M.; Meeeeeeee, M.; Meee, M.; Meee, M. M.; Meeee, M. M., M. Meeeeeeee. Meee., (8888) 888, 888. |
| [260] | Meeeeeee, M.; Meeeeeeeee, M.; Meeee, M.; Meeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [261] | Meeeeeeeee, M.; Meeeeeeee, M.; Meeee, M.; Meeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [262] | Meeeee, M. M.; Meee, M., Mee. Meee., (8888) 8, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 8888.
- 8.Meeeee-Meee, (8888) 8/8e, 8888.
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