Tetrazoles azotetrazoles

SjS Diphenyl-l, l azotetrazole (Called 1.1 -Azo-S -diphenyl-tetrazol by Stolle),... 

Interest in mercury(II) tetrazolates, notably Hg(5-02N-tta)2, as detonators (12, 190) has prompted thermal decomposition studies on mercury salts of 5-nitrotetrazole (34) and 5,5 -azotetrazole (169). Cycloaddition of methyl isocyanide to Hg(N3)2(PPh3)2 under mild conditions yields the C-bonded tetrazolate complex Hg(l-Me-tta)2 (15). Mercury(II) adducts HgX2(l,5-pmtta) (X = Cl, Br, or CN) and Hg(N03)2(l,5-pmtta)2 have been described (174, 236). 

Azotetrazoie (or Bis-5,5 -azotetrazole). See in Voi 1, A659-R to A660-L and the following Addnl Refs 1) H. Morisson, Chemistry of Tetrazole Explosives Derivatives , IntSymp on Utilisation Des Elements Pyrotechniques et Expiosifs Dans Les Systemes Spatiaux , Tarbes (Fr), Dunod (1968) translated by M. Blais, US Army ARRADCOM, Dover (1970) [The impact sensy of various bis-5-azotetrazole salts is presented in Table 7, below... 

Infra-red spectra of the sodium, 1,1r lead, and l,r silver salts of 5,5 -azotetrazole are included] 4) A.T. Thomas R.J. Wiliiams, Fuse Heads , USP 3763783 (1973) CA 80, 17084 (1974) (Electrically initiated (by resistance-wired bridges) fuse heads contg Pb-Azo-tetrazole are claimed in this patent. Thus, typically, sufficient wet Pb-Azotetrazole particles 6—10 microns long and 1—2 microns wide to give 8.08g of dry Pb-Azotetrazole, adjusted to include 2.0g w and 5cc of an aq suspension contg 5% methyl cellulose, is mixed to give a smooth paste. Bridge wires are then immersed in the paste, withdrawn, and the fuse heads so formed are allowed to dry]... 

Under the action of chlorine on l-amino-5-aryltetrazoles in alkaline medium, Stolle obtained compounds he described as l,r-azotetrazoles 354 (33JPR1). These results need reinvestigation. If confirmed, compounds 354 will be the first known tetrazole tetrazenes. 

Heats of formation of hydrazinium [75], ammonium 5,5 -azotetrazola-tes [79], and guanidinium [24,80], were measured as AH =+ 858, + 443, and +410kjmol respectively. In order to compare these properties with azotetrazolates that contain heterocyclic cations, imidazolium, tria-zolium, and tetrazolium derivatives were synthesized and characterized (Scheme 18) [81]. Surprisingly, while most azotetrazolates exhibit melting points in excess of 160 °C, [bis(l-butyl-3-methyl-imidazolium)] 5,5 -azo-tetrazolate (68a) was a liquid at 25 °C with a melting point of 3 C, similar to its 3,5-dinitrotetrazolate analog [46]. 

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