Nitrosation compounds

An N-nitrose compound that is unstable is obtained by the effect of dinitrogen trioxide on caproiactam at a low temperature. The compound detonates when the medium is not cooled enough. 

N. Loprieno. Vegetables inhibit, in DC209 vivo, the mutagenicity of nitrite combined with nitrosable compounds. MutatRes 1983 120(2/3) 145-150. 

Nitrosated compounds have become of high interest since the dem onstration of hepatoxicity of dimethylnitrosamine (527). Recognition of nitrosamines, a class of compounds (528-535) that might be associated with cured meat products, smoked fish products, tobacco products, cer-... 

The purging of nitrogen oxides from exhaust gases (913) and treatment of smoking materials (914) with ascorbates are of interest, particularly the latter, wherein a lower production of potentially carcinogenic nitrosated compounds may result if the application were to be put into effect. 

Incompatible with strong oxidizers acids, water (slowly decomposes, forming amine and carbon disulfide). Reaction with nitrosating compounds (i.e., nitrogen oxides, nitrosyl chloride, nitrite esters, metal nitrates and nitroso compounds, etc.) can cause the formation of carcinogenic N-nitrosodiethylamine. 

AI3-15639 (75-50-3) Extremely flammable liquefied gas [flash point 20°F/-6°C (25% solution in H2O) 41°F/5°C]. A medium-strong organic base. Violent reaction with strong oxidizers, bromine, strong acids, ethylene oxide, halogenated compounds, nitrosating compounds, triethynylaluminum. Incompatible with methyl trichloroacetate. Reacts with mercury, forming shock-sensitive explosive material. Attacks chemically active metals aluminum, copper, tin, zinc, and their alloys. 

The last-mentioned disadvantage of deaminations of amines with nitrosating compounds in aqueous and other protic solvents is, of course, not present if N-nitroso amides and related compounds discussed earlier (7.10, and footnote on p. 246, concerning White s pioneering work) are used in aprotic solvents. 

The key intermediate in all the proposed mechanisms is 2-nitrosocyclohexanone, and thus the most significant HNO3 property utilized is its nitrosating power. In fact, nitric acid acts as an oxidizing agent only in secondary reactions that occur only in the presence of previously nitrosated compounds. Oxidation via the formation of adipomononitrolic acid (AMNA, paths 1 and 2) requires an oxidative step to 2-nitrocyclohexanone and a second nitrosating step to 2-nitroso 2-nitro cyclohexanone. This seems to be the favourite path in the presence of concentrated nitric acid... 

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