Nitramines

Nitramines

 

(N-nitroamino compounds), organic compounds whose molecules contain an —NO2 group bound to a nitrogen atom. Nitramines may be primary, RNHNO2, or secondary, RRʹNNO2 (where R and Rʹ are alkyl or aryl groups).

Monoalkyl nitramines are produced by nitration of N-acylated primary amines (1) or dichloroamines (2) with a nitrating mixture—for example,

(1) CH3NHCO2CH3 → CH3N(NO2)CO2CH3 → CH3NHNO2

Secondary aliphatic nitramines are formed by treating the corresponding amines with a mixture of nitric acid and acetic anhydride or with nitronium fluoboride. Aryl nitramines are synthesized by direct nitration of the corresponding amines or oxidation of diazonium salts.

Aromatic nitramines are usually solids; aliphatic nitramines are liquids or fusible solids. Under the action of acids, primary aliphatic nitramines decompose into the corresponding alcohols and nitrous oxide. Secondary nitramines are resistant to the action of acid even at 100°C, whereas aromatic nitramines undergo various rearrangements.

Upon reaction with alkalies, most primary nitramines yield salts; secondary aliphatic nitramines having α-hydrogen atoms may decompose to amines and aldehydes:

The lower nitramines are extremely explosive. Some nitramines are used as high explosives—for example, trinitro-phenylmethylnitramine (tetryl), cyclotrimethylenetrinitramine (cyclonite), and cyclotetramethylenetetranitramine (octogen).

REFERENCES

Khimiia nitro- i nitrozogrupp. Edited by H. Feuer. Moscow, 1972. (Translated from English.)
Overberger, C. G., J.-P. Anselme, and J. G. Lombardino. Organicheskie soedineniia so sviaziami azot-azot. Leningrad, 1970. (Translated from English.)

M. M. KRAIUSHKIN

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