Methods for the preparation of various N-substituted oxaazaisowurtzitane derivatives have been generalized in this review. The advantages, drawbacks, and perspectives for the development of the main approaches to the synthesis of these compounds have been discussed. A comparison is provided for the physicochemical and explosive characteristics of energetic compounds containing the frameworks of oxaazaisowurtzitanes, CL-20, and HMX.
Similar content being viewed by others
References
Sysolyatin, S. V.; Lobanova, A. A.; Chernikova, Y. T.; Sakovich, G. V. Russ. Chem. Rev. 2005, 74, 757. [Usp. Khim. 2005, 74, 830.]
Ananikov, V. P.; Khemchyan, L. L.; Ivanova, Yu. V.; Bukhtiyarov, V. I. Russ. Chem. Rev. 2014, 83, 885. [Usp. Khim. 2014, 83, 885.]
Nielsen, A. T.; Chaen, A. P.; Christian, S. L.; Moore, D. W. Nadler, M. P.; Nissan, R. A.; Vanderah, D. J. Tetrahedron 1998, 54, 11793.
Bircher, H. R.; Maeder, P.; Mathieu, J. In Proceedings of the 29th International Annual Conference of ICT, Karlsruhe, Germany, 1998; Karlsruhe, 1998, p. 94.1.
Kleinschmidt, E.; Wanninger, P. DE Patent 4324739.
Clement, D.; Koch, E.-C.; Rudolf, K.; Eigenmann, B. In 10th Seminar New Trends in Research of Energetic Materials, Pardubice, Czech Republic, 25–27 April 2007; Pardubice, 2007, p. 128.
Radacsi, N.; Bouma, R. H. B.; Krabbendam-laHaye, E. L. M.; ter Horst, J. H.; Stankiewicz, A. I.; van der Heijden, A. E. D. M. Propellants, Explos., Pyrotech. 2013, 38, 761.
Risse, B.; Schell, F.; Spitzer, D. Propellants, Explos., Pyrotech. 2014, 39, 391.
Doherty, R. M.; Watt, D. S. Propellants, Explos., Pyrotech. 2008, 33, 4.
Borne, L.; Mory, J.; Schlesser, F. Propellants, Explos., Pyrotech. 2008, 33, 37.
Koch, E.-C. Propellants, Explos., Pyrotech. 2015, 40, 374.
Komarov, V. F.; Kalmykov, P. I.; Boyarinova, N. V.; Markov, V. F. Russ. J. Appl. Chem. 2012, 85, 747. [Zh. Prikl. Khim. 2012, 85, 746.]
Liu, K.; Zhang, G.; Luan, J.; Chen, Z.; Su, P.; Shu, Y. J. Mol. Struct. 2016, 1110, 91.
Bolton, O.; Simke, L. R.; Pagoria, P. F.; Matzger, A. J. Cryst. Growth Des. 2012, 12, 4311.
Gao, B.; Wang, D.; Zhang, J.; Hu., Y.; Shen, J.; Wang, J.; Huang, B.; Qiao, Z.; Huang, H.; Nie, F.; Yang, G. J. Mater. Chem. A 2014, 2, 19969.
Xu, H.; Duan, X.; Li, H. RSC Adv. 2015, 5, 95764.
Goncharov, T. K.; Aliev, Z. G.; Aldoshin, S. M.; Dashko, D. V.; Vasil'eva, A. A.; Shishov, N. I.; Milekhin, Yu. M. Russ. Chem. Bull., Int. Ed. 2015, 64, 366. [Izv. Akad. Nauk, Ser. Khim. 2015, 366.]
Yang, Z.; Li, H.; Zhou, X.; Zhang, C.; Huang, H.; Li, J.; Nie, F. Cryst. Growth Des. 2012, 12(11), 5155.
Gatilov, Yu. V.; Rybalova, T. V.; Efimov, O. A.; Lobanova, A. A. J. Struct. Chem. 2005, 46(3), 566. [Zh. Strukt. Khim. 2005, 46(3), 579.]
Braithwaite, P. C.; Edwards, W. W.; Hajik, R. M.; Highsmith, T. K.; Lund, G. K.; Wardle, R. B. In 29th International Annual Conference of ICT, Karlsruhe, Germany, 30 June – 3 July 1998; Karlsruhe, 1988, p. 62.
Efimov, О. А.; Sysolyatin, S. V.; Budaeva, V. V.; Sivkova, N. A. USSR Author's Invention 235109.
Efimov, О. А.; Popov, N. I.; Sakovich, G. V.; Lobanova, А. А.; Sysolyatin, S. V.; Il'yasov S. G. USSR Author's Invention 230121.
Sysolyatin, S. V.; Sakovich, G. V.; Chernikova, Y. T.; Surmachev, V. N.; Lobanova, A. A. In 37th International Annual Conference of ICT, Karlsruhe, Germany,. June 27–30 2006; Karlsruhe, 2006, p. 141.
Ramakrishnan, V. T.; Vedachalam, M.; Boyer, J. H. Heterocycles 1990, 31, 479.
Highsmith, T. K.; Edwards, W. W.; Wardle, R. B. US Patent 5498711.
Ghaderi, H.; Zolfigol, M. A.; Bayat, Y.; Zarei, M.; Noroozizadeh, E. Synlett 2016, 27, 2246.
Kharaghiosoff, K.; Klapötke, T. M.; Michailovski, A.; Nöth, H.; Suter, M.; Holl, G. Propellants, Explos., Pyrotech. 2003, 28, 1.
Hanks, J.; Highsmith, T.; Lesley, M.; Sanderson, A.; Warner, K.; Worthington, J. In Insensitive Munitions and Energetic Materials Technology Symposium, Orlando, USA, 10–13 March 2003; Orlando, 2003, p. S5A-P3.
Currie, A.C.; Dinwoodie, A. H.; Fort, G.; Thompson, J. M. C. J. Chem. SOC. (C) 1967, 491.
Maksimowski, P.; Golofit, T. J. Energ. Mater. 2013, 31, 224.
Wardle, R. B.; Hajik, R. M.; Hinshaw, J. C.; Highsmith, T. K. US Patent 6107483A.
Jalovy, Z.; Maty, R. In The Influence of Reactions Conditions on TEX Synthesis, Vth Seminar, New Trends in Research of Energetic Materials, Pardubice, Czech Republic, 24–25 April 2002; Pardubice, 2002, p. 92.
Jacob, G.; Lacroix, G.; Destombes, V. In From International Annual Conference of ICT, 31st (Energetic Materials), Karlsruhe, Germany, 2000; Karlsruhe, 2000, p. 106.
Kalashnikov, A. I.; Sysolyatin, S. V.; Shein, N. V. Polzunovsky Vestnik 2013, 3, 42.
Kalashnikov, A. I.; Kadulin, V. V.; Sysolyatin, S. V.; Chernikova, Yu. T.; Lobanova, А. А. RU Patent 2355693.
Kalashnikov, А. I.; Sysolyatin, S. V.; Chernikova, Yu. T.; Kadulin, V. V.; Lobanova, А. А. Polzunovsky Vestnik 2007, 3, 48.
Duda, M.; Maksimowski, P.; Skupinski, W. In New Trends in Research of Energetic Materials: Proceedings of the 9th Seminar Held at the University of Pardubice, the Czech Republic, University of Pardubice, Faculty of Chemical Technology, Institute of Energetic Materials, 19–21 April 2006; Pardubice, 2006, p. 561.
Paromov, A. E.; Sysolyatin, S. V.; Gatilov, Y. V. J. Energ. Mater. 2017, 35, 363.
Sysolyatin, S. V.; Paromov, A. E. In Collection of abstracts from XII International conference HEMs-2016 ''High-energy Materials: Demilitarization, Antiterrorism, and Civilian Applications'' [in Russian], Tomsk, Russia, September 7–10, 2016; Tomsk, 2016, p. 9.
Efimov, О. А.; Lobanova, А. А.; Popov, N. I.; Sakovich, G. V. USSR Author's Invention 231070.
Sysolyatin, S. V.; Lobanova, A. A.; Chernikova, Y. T. In International Conference ''Modern Problems of Organic Chemistry'', Novosibirsk, 27–30 September 2001; Novosibirsk, 2001, 104.
Sysolyatin, S. V.; Surmachev, V. N.; Lobanova, A. A.; Chernikova, Y. T.; Sakovich, G. V. In 5th International High-Energy Materials Conference and Exhibit, DRDL, Hyderabad, 23–25 November 2005; Hyderabad, 2005, p. 101.
Kerscher, T.; Klapötke, T.; Krumm, B.; Polborn, K.; Scherr, M. J. Fluorine Chem. 2006, 127, 1030.
Simpson, R. L.; Urtiew, P. A.; Ornellas, D. L.; Moody, G. L.; Scribner, K. J.; Hoffman, D. M. Propellants, Explos., Pyrotech. 1997, 22, 249.
Sakovich, G. V.; Sysolyatin, S. V.; Kozirev, N. V.; Makarovets, N. A. RU Patent 2252925.
Nielsen, A. T. US Patent 5693794.
Kozyrev, N. V.; Sysolyatin, S. B.; Sakovich, G. V. Combust., Explos. Shock Waves 2006, 42, 486. [Fizika Goreniya i Vzryva 2006, 42(4), 131.]
Zeman, S.; Atalar, T. J. Energ. Mater. 2009, 27, 217.
Lund, G. K.; Highsmith, T. K.; Brathwaite, P. C.; Wardle, R. B. US Patent 5529649.
Vagenknecht, J.; Marecek, P.; Trzcinski, W. A. J. Energ. Mater. 2002, 20, 245.
Deshmukh, M. B.; Borse, A. U.; Mahulikar, P. P.; Dalal, D. S. Org. Process Res. Dev. 2016, 20, 1363.
Walsh, M. E.; Jenkins, T. F.; Thorne, P. G. J. Energ. Mater. 1995, 13, 357.
Lee, J.-S.; Hsu, C.-K.; Chang, C.-L. Thermochim. Acta 2002, 392–393, 173.
Stepanov, R. S.; Kruglyakova, L. A. Russ. J. Gen. Chem. 2010, 80, 316. [Zh. Obshch. Khim. 2010, 80, 291.]
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(6/7), 630–637
Rights and permissions
About this article
Cite this article
Paromov, A.E., Sysolyatin, S.V. Oxaazatetracyclo[5.5.0.03, 10.05, 8]Dodecanes – a Promising Foundation for the Design of Thermally Stable, High-Density Energetic Compounds. Chem Heterocycl Comp 53, 630–637 (2017). https://doi.org/10.1007/s10593-017-2105-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-017-2105-x