Ozone reactions with aliphatic amines

While primary aliphatic amines are converted to nitro compounds on reaction with ozone these reactions are accompanied by numerous by-products.Such side-reactions are largely suppressed by first dissolving the amine onto silica gel followed by passing a stream of 3 % ozone in oxygen through the solid at -78 °C under anhydrous conditions, where yields of between 60 and 70 % are reported. This route has been used to synthesize the energetic cyclopropane (65) from the diamine (64) (Table 1.7). ... 

ACETIC ACID, ETHENYL ESTER (108-05-4) Forms explosive mixture with air (flash point 18°F/-7°C). Polymerizes readily if not inhibited elevated temperatures, the influence of light, air, oxygen, water, or peroxides can initiate reaction. Must be stabilized (hydro-quinone or diphenylamine is recommended) to prevent polymerization. Violent reaction with strong oxidizers. Reacts with nonoxidizing mineral acids, strong acids, ammonia, aliphatic amines, alkanolamines, bases, azo compounds, oleum, ozone (forms explosive vinyl acetate... 

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