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Kibayashi, C.; Yamazaki, N., Science of Synthesis, (2007) 30, 8.
In general, the oxidation of aldehyde-derived hydrazones with lead(IV) acetate in acetic acid solution usually gives N-acyl-N′-acetylhydrazines, whereas the oxidation of ketone-derived hydrazones normally affords diazenyl acetates posessing an O–C–N function.[3] For example, the oxidation of hydrazone 12 with lead(IV) acetate leads to the corresponding gem-diazenyl acetate 13.[4] In this reaction, the diastereoselectivity is high and no detectable epimer is formed (Scheme 4). Similarly, the oxidation of cyclohex-2-enone methylhydrazone 14 with lead(IV) acetate affords the diazenyl acetate 15 in 70% yield.[5]
Me eeeeeeee ee eee eeee eeeeeeeee eeeee,[8] eee eeeeeeee ee eeeeeeee-eeeeeee eeeeeeeeee 88, eeeee eeee eeeeee ee eee eeeeeeee-eeeeeeeeeee 8-eeeeeeeeeee ee 8,8-eeeeeeeeeeeee eeeeeeeeeeee, eeee eeee(MM) eeeeeee eeeee eeeeeeee eeeeeeee 88 ee eeeeee eeeeeee eeee 88 ee 88%.[8]
Meeeee 8 Meeeeeeeeee ee e Meeeeeee Meeeeee ee Meeeeeeee ee Meeeeeeeee[8–8]
Meeeeee eeeeee ee eeeeeeeee eeeeeee M,M-eeeeeee eeeeeee eee eeeeeeee ee e eeeeeeeeeee ee e M=M eeee ee ee eee eeeeeeeee ee ee eeeee 88 eeee eeeeeee eeeeeeeeeeeee ee eee eeeeeeee ee eeeeeee. Meeeeeeeee eeeeeeeeeeee eeeee 88 ee 88% eeeee (Meeeee 8).[8]
Meeeee 8 Meeeeeeeeee ee ee α-Meeeeeeeeeeeeee[8]
Meeeeeeeeeee Meeeeeeee
[(M)-(8,8-Meeeeeeeeeeee)eeeeeeee]eeeeee Meeeeee [88, Me8 = 8,8-(M8M)8M8M8; M8 = M]:[8]
M eeee ee eee eeeeeeeee 88 (8 e, 8.88 eeee) ee MeMM (88 eM) eeeeeeeeee Me8M (8 eM) eee eeeeeee eeee Me(MMe)8 (8.88 e, 8.88 eeee) eee eeeeeee eee 88 eee ee ee. Meeee eeeeeee ee eee eeee eeee, eee eeee eee eeeeeee ee 888 eM eeee M8M eee eeeeeeeee eeee Me8M (8 × 888 eM). Mee eeeeeeee eeeeeeee eeee eeeeee eeee M8M (8 × 888 eM), eeeeeee eeee ee MeMMM8 eeee (888 eM), eee eeeeeeeeeeee eeeeee ee eeee 88 ee eeeeee eeeeeee; eeeee: 8.88 e (88%); ee 88–88°M; MM ν̃eee: 8888 ee−8; 8M MMM (MMMe8, δ): 8.88, 8.88, 8.88 (8M, eeee), 8.88 (e, 8M, M = 8 Me), 8.88 (8M, MM8), 8.88 (e, 8M, Me).
References
| [3] | Meeeee, M. M.; Meeee, M. M.; M'Meeeee, M. M. M., Meee. Mee., (8888) 88, 88. |
| [4] | Meeeeeee, M. M. M.; Meeeeeeeeee, M.; Meeeeeee, M., Meee. Meee. Meee, (8888) 88, 88. |
| [5] | Meeeee, M. M.; MeMeeeeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
| [6] | Meeeee, M. M.; Meee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 88. |
| [7] | Meeeeeee, M.; Meee, M.; Meeeee, M., Meeeeee, (8888), 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88e8, 88.
- 8.Meeeee-Meee, (8888) M 88e8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 88.
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