Products from the Reaction of Dinitrotetramethylbenzenes with Fuming Nitric Acid. A New Route to Some Polynitro Carbonyl Compounds
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概要
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Reaction of dinitrotetramethylbenzenes with fuming nitric acid has been investigated. 5,6-Dinitro-1,2,3,4-tetramethylbenzene undergoes a slow oxidation to give 2,3,4,5-tetranitro-2,3,6,6-tetramethylcyclohex-4-enone in 82–87% yield, which is thermally unstable and upon heating readily converted into 4,5-dinitro-2,3,6,6-tetramethylcyclohexa-2,4-dienone losing two molecules of nitrogen dioxide. 4,6-Dinitro-1,2,3,5-tetramethylbenzene reacts readily with cold fuming nitric acid, giving 2,6-dinitro-3,4,5-trimethylbenzaldehyde in 76–84% yield, together with small amounts of 2,6-dinitro-3,4,5-trimethylphenylnitromethane, 2,6-dinitro-3,4,5-trimethylbenzoic acid, and 2,6-dinitro-3,4,5-trimethylbenzyl alcohol. 3,6-Dinitro-1,2,4,5-tetramethylbenzene is stable towards the action of fuming nitric acid, but is slowly converted into 3,6-dinitro-2,4,5-trimethylbenzyl nitrate on being heated with mixed acid at 40–50°C. The mode of formation of unusual products is briefly discussed.
- 公益社団法人 日本化学会の論文
著者
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Suzuki Hitomi
Deparment Of Chemistry School Of Science Kwansei Gakuin University
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Nakamura Kiyomi
Department of Chemistry, Faculty of Science, Kyoto University
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