Abstract
Fluorenone and benzophenone oxime react in glacial acetic acid with lead tetraacetate to give parent ketones, geminal dinitromethanes, iminyl ketal derivatives (9,9-difluorenylideniminoxylfluorene and 1,1-bis(diphenylmethylideniminoxyl)-diphenylmethane), and minor amounts of oxime O-acetate. Benzophenone nitrimine is also formed but only in the absence of oxygen. Side reactions due to nitric oxide, oxygen, and nitrogen dioxide take place. Separate studies with these oxidizing agents have therefore been conducted. The lead tetraacetate oxidation of these oximes in methylene chloride (or any other solvent) is complete with a half-mole equivalent of lead tetraacetate, is insensitive to molecular oxygen, and affords mainly parent ketone and ketazinemonoxides. No ketazine-bis-N-oxides, obtained from the ferricyanide oxidation of these oximes, are formed. The model oximes, benzil anti-monoxime, xanthone oxime, and indanone oxime have been studied in the light of these observations. Mechanisms involving iminoxyl radicals have been postulated for all reactions studied.
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