Hydrazones sodium perborate

SAMP-Hydrazones derived from ketones may also be cleaved by treatment with three equivalents of sodium perborate tetrahydrate at pH 7 in water/rert-butyl alcohol at 60 °C. Hydrolysis of aliphatic derivatives is effected in 4-24 hours and reactions yielding aromatic ketones proceed within 2- 3 days. This cleavage reaction furnishes the desired ketones chemoselectively in the presence of olefinic double bonds in 85-95% yield (cyclopentanone 70% yield)30. 

Alkylated Ketones by Cleavage of Alkylated SAMP-Hydrazones General Procedure with Sodium Perborate Tetrahydrate30 ... 

A new method for cleavage was recently reported by Enders. Treatment of the hydrazone with three equivalents of sodium perborate regenerate the carbonyl compound in 70-95% yield according to equation (36). This oxidative cleavage was chemoselective and left carbon-carbon double bonds intact. This chemoselectivity plus the neutral hydrolytic conditions and the low cost of the oxidant make this method quite attractive, liie main disadvantage of this method is the relatively long reaction time required, ranging from 4-24 h for aliphatic ketone hydrazones to 2-3 d for aromatic ketone hydrazones. 

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