Abstract
For the example of a salt of azotetrazole, for the first time we have investigated the azotetrazole-1,2,3,4,5-pentazine tautomerism. Upon treatment of an excess of the disodium salt of azotetrazole with dilute sulfuric acid, we isolated 5-substituted tetrazole, which on the basis of analysis data (with introduction of the 15N isotope into the compound) and study of the chemical properties with sufficiently high probability of assigning the structure of the first representative of the previously unknown class of compounds of the pentazine mesoion: the tetrahydrate of the sodium salt of the 2-(tetrazolyl-5)-6-imino-1,2,3,4,5-pentazine mesoion. We synthesized the dehydrate of the sodium and silver salts of 5-azodiazomethanotetrazole; using derivatography, we have studied the properties of the isolated compounds.
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A. G. Mayants, V. N. Vladimirov, N. M. Razumov, and V. A. Shlyapochnikov, Zh. Org. Khim., 27, 2450 (1991).
A. G. Mayants, L. M. Tishchenko, V. N. Vladimirov, and V. A. Shlyapochnikov, Khim. Geterotsikl. Soedin., No. 10, 1351 (1992).
A. G. Mayants, V. S. Klimenko, V. V. Erina, K. G. Pyreseva, S. S. Gordeichuk, V. N. Leibzon, V. S. Kuz'min, and Yu. N. Burtsev, Khim. Geterotsikl. Soedin., No. 8, 1067 (1991).
R. C. Elderfield (ed.), Heterocyclic Compounds [Russian translation], Vol. 8, Mir, Moscow (1969), pp. 53–56, 74, 75.
S. Patai (ed.), The Chemistry of the Azido Group, Interscience, London.
A. G. Mayants, N. A. Klinova, and S. S. Gordeichuk, Khim. Geterotsikl. Soedin., No. 7, 945 (1987).
D. H. R. Barton and W. D. Ollis (eds.), Comprehensive Organic Chemistry [Rssian translation] Vol. 8, Khimiya, Moscow (1985), pp. 194, 698, 699.
M. N. Glukhovtsev, B. Ya. Simkin, and V. I. Minkin, Khim. Geterotsikl. Soedin., No. 2, 250 (1988).
M. N. Glukhovtsev, B. Ya. Simkin, and V. I. Minkin, Zh. Org. Khim., 24, 486 (1988).
E. G. Gal'pern, I. V. Stankevich, A. L. Chistyakov, V. B. Shur, and M. E. Vol'pin, Dokl. Akad. Nauk, 302, 1384 (1988).
A. M. Churakov, S. L. Ioffe, Yu. A. Strelenko, and V. A. Tartakovskii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 718 (1990).
V. A. Chuiguk, Khim. Geterotsikl. Soedin., No. 1, 7 (1983).
G. A. Wander Werf and V. L. Heasley, J. Org. Chem., 31, 3534 (1966).
C. G. Overberger, J. P. Anselme, and J. G. Lombardino, Organic Compounds with Nitrogen—Nitrogen Bonds [Russian translation], Khimiya, Leningrad (1970), p. 117.
V. P. Krivopalov, V. I. Mamatyuk, and V. P. Mamaev, Khim. Geterotsikl. Soedin., No. 12, 1648 (1990).
L. J. Bellamy, New Data on IR Spectra of Complex Molecules [Russian translation], Mir, Moscow (1971), p. 73.
V. I. Mel'nikov and K. K. Pivnitskii, Zh. Org. Khim., 26, 78 (1990).
E. Schmitz, Three-Membered Rings with Two Heteroatoms [Russian translation], Mir, Moscow (1970), pp. 210–212.
S. D. Isaev, G. T. Zhalnina, Z. N. Murzinova, S. I. Lastovenko, and A. G. Yurchenko, Zh. Org. Khim., 24, 142 (1988).
A. G. Mayants, K. G. Pyreseva, and S. S. Gordeichuk, Zh. Org. Khim., 24, 884 (1988).
P. F. Bubnov, Initiating Explosives and Initiation Devices [in Russian], Izdat. Oboron. Prom., Moscow (1940), pp. 310, 311, 314.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 468–475, April, 1993.
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Mayants, A.G., Vladimirov, V.N., Shlyapochnikov, V.A. et al. Synthesis of 5-substituted tetrazoles based on the disodium salt of azotetrazole. investigation of the azotetrazole-2-(tetrazolyl-5)-6-imino-1,2,3,4-pentazine mesoion tautomerism. Chem Heterocycl Compd 29, 395–401 (1993). https://doi.org/10.1007/BF00529876
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DOI: https://doi.org/10.1007/BF00529876