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High-density energetic mono- or bis(oxy)-5-nitroiminotetrazoles.

In the last decade, the investigation of energetic tetrazoles— cyanotetrazole, aminotetrazole, azidotetrazole, nitrotetrazole, and nitroiminotetrazole—has led to major developments in the area of high-energetic materials by many research groups. Several exciting classes of 5-substituted tetrazole moieties are introduced in the literature. Tetrazoles can be protonated to form tetrazolium salts or deprotonated to give tetrazolates. While deprotonation increases the thermal stability of tetrazoles, protonation can lower the decomposition temperature. These energetic materials based on high nitrogen content are derived from their high heats of formation due to the large number of N N and C N bonds. The combination of a tetrazole ring with energetic substituent groups containing oxygen atoms, such as nitro groups, nitrate esters, or nitramine, is of interest leading to excellent oxidizers. Current research issues in the field of high energetic materials include increasing oxygen content, which may result in the replacement of ammonium perchlorate in an effort to decrease pollution. Organic 5-nitrotetrazole derivatives, especially for synthesis of the highly energetic 1-methyl-5-nitrotetrazole, were synthesized in good yields. These were calculated to be endothermic with heats of formation of 2.16 kJg , which was assessed by means of standard tests and quantum chemical calculations. In addition, the highly energetic, nitrogen-rich 1-methyl-5-nitroiminotetrazole and its salts can easily be obtained by nitration of aminotetrazole followed by metathesis reactions using silver 1-methyl-5-nitroiminotetrazolate and the guanidinium family of chlorides in aqueous solution with high yields. Although 5-nitroiminotetrazole derivatives and their salts are energetic materials with high nitrogen content, they show good stabilities towards friction and impact, and good thermal stability. The development of new energetic compounds with similar attractive properties exhibit significant promise in optimizing environmentally benign replacements for toxic materials. In the past few years, the most convenient route to 1substituted 5-aminotetrazole is the addition of amine or hydrazine to cyanogen azide, which was found to be an efficient reagent for the synthesis of readily purified 1substituted 5-aminotetrazoles from primary amines under non-catalytic mild conditions. Nitration of these aminotetrazoles using 100% nitric acid has been shown to form mono-, di-, or trisubstituted nitroiminotetrazole derivatives. With these features in mind, our group became interested in examining the analogous chemistry using alkoxy amine derivatives. Here we describe the work leading to a series of nitroiminotetrazole derivatives of oxy nitroiminotetrazoles and their salts, with potentially significant physical and energetic properties. The aim of our study was to elucidate the structures in the crystalline state using X-ray diffraction analysis and to find new, potent oxygenand nitrogen-rich tetrazoles. Alkoxy 5-nitroiminotetrazolates may be of interest as a new class of ionic energetic materials, which have good thermal stabilities, high densities, good oxygen balance, and high heats of formation and which are realizable in high yields though straightforward routes. The synthesis of 1-methoxy-5-aminotetrazole (2) was achieved from the reaction of cyanogen azide with methoxy amine (obtained by neutralization of 1 with sodium hydroxide) (Scheme 1). At ambient temperature, nitration of amino-