Oxidation of Ketone Derivatives

The treatment of ketimines (Schiff bases) with peroxyacetic acid gives oxaziridines (equation 453) [1178.  

Oximes are either oxidized to nitro compounds [823] or converted into their respective parent ketones [422, 427, 527, 660]. Oxidation to the parent ketones applies also to semicarbazones 427, 527], dimethylhydrazones [528, 529], tosylhydrazones [527, 528, 529], phenylhydrazones [527], p-nitrophenylhydrazones [527], and 2,4-dinitrophenylhydrazones [527] (equations 454-456). 

Because such exotic reagents as those shown in equations 455 and 456 are not readily available, cleavage by ozone may be preferred [ii79]. 

Ketone derivatives whose oxidations have wide applications in synthesis are hydrazones and vicinal dihydrazones. Hydrazones are transformed into diazo compounds, and vicinal dihydrazones are converted into acetylenes. By far the most widely used oxidant is yellow mercuric oxide 

Examples of the oxidation of aliphatic hydrazones are the conversion of acetone hydrazone into 2-diazopropane [386, 392], of hexafluoroacetone hydrazone into 2-diazohexafluoropropane [445], of 4-octanone hydrazone into 4-diazooctane [386], and of the hydrazone of diethyl mesoxalate into diethyl diazomalonate [935] (equations 457 and 458). 

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ASYMMETRIC OXIDATION OF KETONE-DERIVED ENOLATES USING (+)-(2R,8aS)-10-(CAMPHORYLSULFONYL)OXAZIRIDINE... 

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