Ponzio reaction

It was first prepd by Milone Massa (Ref 2) by nitrating phenyldinitromethane with strong nitric acid (a i.52g/cc). Fieser et al (Ref 3) prepd it using two methods a) nitration of phenyldinitromethane and b) by direct synthesis using the Ponzio reaction in which an ethereal soln of m-nitrobenzaldoxime is added dropwise and under reflux to an ethereal soln of nitrogen peroxide ... 

Ponzio Reaction. The formation of phenyl-dinit romethane from benzaldoxime by oxidation with nitrogen dioxide in eth (Refs 1 2) CH=NOH CH(N02)2... 

The Ponzio reaction provides a useful route to gem-dinitro compounds and involves treating oximes with a solution of nitrogen dioxide or its dimer in diethyl ether or a chlorinated solvent. The Ponzio reaction works best for aromatic oximes where the synthesis of many substituted aryldinitromethanes have been reported. Compound (56), an isomer of TNT, is formed from the reaction of dinitrogen tetroxide with the oxime of benzaldehyde (55) followed by mononitration of the aromatic ring with mixed acid. Yields are usually much lower for aliphatic aldoximes and ketoximes. " The parent carbonyl compound of the oxime is usually the major by-product in these reactions. 

The use of dinitrogen pentoxide in the Ponzio reaction for the oxidation-iutration of oximes to em-dinitro groups has been reported by Russian chemists. Millar and co-workers extensively investigated these reactions and reported the synthesis of 2,4,5,7,9,9-hexanitrofluorene (2), a thermally stable explosive with an oxygen balance better than TNT. Other energetic materials containing gem-dinitro functionality were synthesized from the oximes of acetophenone, 4-nitroacetophenone, a-nitroacetophenone and 2-hydroxyacetophenone. 

The oxidation of oximes by lead(IV) acetate, chlorine and other oxidants results in the formation of a-substituted nitroso compounds R R C(X)NO by attack of the oxidant at carbon. This is also the reaction commonly observ with dinitrogen tetroxide (the Ponzio reaction), the products being gem-... 

Poltdo reaction. In the Ponzio reaction, dinitrogen tetroxide in ether converts benzaldoxitne into phenyldinitromethane. In an improved procedure a fume-off is... 

Other references related to the Ponzio reaction are cited in the literature. ... 

Ponzio Reaction Potier-Polonovski Reaction Prevost Reaction... 

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