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Mechanism of nitric acid oxidation of acetophenone to dibenzoylfurazan 2-oxide, benzoic acid, and benzoylformic acid
J. Chem. Soc., Perkin Trans. 2 Pub Date : 1985 , DOI: 10.1039/p29850001643
Hiroshi Tezuka , Megumi Kato , Yukito Sonehara

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.

中文翻译:

硝酸将苯乙酮氧化为二苯甲酰呋喃二氧化物,苯甲酸和苯甲酰甲酸的机理

在水性有机溶剂中,用稀硝酸将苯乙酮,苯甲酰甲醛肟和苯甲酰硝基甲烷氧化为二苯甲酰呋喃二氧化物,苯甲酸和苯甲酰甲酸。在78%的硝基甲烷水溶液中将苯甲酰基硝基甲烷进行硝酸氧化,在大约2小时内得到二苯甲酰基呋喃山2-氧化物产率为70%,表明苯甲酰基硝基甲烷被亚硝化,得到硝基苯甲酰基甲醛肟(苯甲酰基甲腈酸)。类似地,认为苯乙酮被硝基离子攻击而生成苯甲酰基甲醛肟,而不是通过与二氧化氮硝化而生成的苯甲酰基硝基甲烷。苯甲酰甲酸和苯甲酸衍生自硝酸及其氧化产物。
更新日期:2017-01-31
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