Ralf Haiges - Energetic High-Nitrogen Compounds: 5-(Trinitromethyl)-2H-tetrazole and -tetrazolates, Preparation, Characterization, and Conversion into 5-(Dinitromethyl)tetrazoles.

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  Publication Details (including relevant citation   information): Haiges, Ralf, Christe, Karl O., Inorg.   Chem., 2013, 52 (12), pp 7249-7260

  Abstract: A convenient access to   5-(trinitromethyl)-2H-tetrazole (HTNTz) was developed, based on   the exhaustive nitration of 1H-tetrazole-5-acetic acid, which was   prepd. from Et cyanoacetate and HN3 in a 1,3-dipolar cycloaddn.   reaction, followed by basic hydrolysis. HTNTz was converted into   the ammonium, guanidinium, rubidium, cesium, copper, and silver   5-(trinitromethyl)-2H-tetrazolates. The ammonia adducts of the   copper and silver salts were isolated. The reaction of HTNTz with   hydrazine and hydroxylamine gave hydrazinium   5-(dinitromethyl)tetrazolate and hydroxylammonium   5-(dinitromethyl)-1H-tetrazolate, resp. Acid treatment of both   5-(dinitromethyl)tetrazolates gave   5-(dinitromethylene)-4,5-dihydro-1H-tetrazole, which was   converted into potassium 5-(dinitromethyl)-1H-tetrazolate by   reaction with K2CO3. All prepd. compds. were fully characterized   by 1H, 13C, 14N, and 15N NMR spectroscopy and x-ray crystal   structure detn. Initial safety testing (impact, friction, and   electrostatic sensitivity) and thermal stability measurements   (DTA) were also carried out. The 5-(trinitromethyl) and   5-(dinitromethyl)tetrazoles are highly energetic materials that   explode upon impact or heating. [on SciFinder(R)]

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