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Mechanism of nitric acid oxidation of acetophenone to dibenzoylfurazan 2-oxide.pdf

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Mechanism of nitric acid oxidation of acetophenone to dibenzoylfurazan 2-oxide

J. CHEM. SOC. PERKIN TRANS. II 1985 1643 Mechanism of Nitric Acid Oxidation of Acetophenone to Dibenzoylfurazan 2- Oxide, Benzoic Acid, and Benzoylformic Acid Hiroshi Tezuka, Megumi Kato,t and Yukito Sonehara Faculty of Liberal Arts and t Faculty of Science, Shinshu University, Asahi, Matsumoto 390, Japan Acetophenone, benzoylformaldehyde oxime, and benzoylnitromethane were oxidised with dilute nitric acid to dibenzoylfurazan 2-oxide, benzoic acid, and benzoylformic acid in aqueous organic solvents. The nitric acid oxidation of benzoylnitromethane in 78% aqueous nitromethane gave dibenzoylfurazan 2- oxide in ca. 70% yield, suggesting nitrosation of benzoylnitromethane to give nitrobenzoylformaldehyde oxime (benzoylformonitrolic acid). Similarly, acetophenone is considered to be attacked by the nitrosonium ion to give benzoylformaldehyde oxime, instead of benzoylnitromethane by nitration with nitrogen dioxide. Benzoylformic acid and benzoic acid are derived from the nitrolic acid and its oxidation product. It is known that acetophenones are oxidised by nitric acid to give furazan 2-oxides, and the reaction has often been used as a convenient preparative method for various kinds of diacyl- furazan 2-0xides.~ However, the detailed reaction mechanism remains to be studied. Snyder and Boyer suggested benzoylformaldehyde oxime rather than benzoylnitromethane as an intermediate in the nitric acid oxidation of acetophenone, because dibenzoylfurazan 2-oxide was formed, in yield substantially lower than that obtained from acetophenone, when benzoylnitromethane was treated under the conditions employed with acetophenone. However, it was found in the present study that the nitric acid oxidation of benzoyl- nitromethane gave an amount of dibenzoylfurazan 2-oxide comparable with that obtained from acetophenone. It is known that furazan 2-oxides are obtained from nitrolic acids3 Benzoylformonitrolic acid which is a presumed intermediate in the present