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The results of our studies on the reactivity of 3,4-bis(4'-nitrofurazan-3'- yl)furoxan (BNFF), with some O- and N-nucleophiles are presented. It is shown that both nitro groups of BNFF can be easily replaced by nucleophiles. Depending on the identity of the nucleophile, BNFF may be transformed into two types of 1,2,5-oxadiazole derivatives, notably 4-R substituted bis(4-R-furazan-3-yl) furoxanes or 7-R substituted 7H(7R)-tris[1,2,5]oxadiazolo[3,4-b:3',4-d:3",4"-f]]azepine-1-oxides - a new heterocyclic system comprised of an azepine ring annelated with three 1,2,5-oxadiazole rings.
Słowa kluczowe
Rocznik
Tom
Strony
329--342
Opis fizyczny
Bibliogr. 30 poz., fig., tab.
Twórcy
autor
autor
autor
- Special Design and Construction Bureau SDCB "Technolog", Sovetsky prosp. 33-A, 192076 Saint Petersburg, Russia, stepanoff@pisem.net
Bibliografia
- [1] Ravi P., Badgujar D.M., Gore G.M., Tewari S.P., Sikder A.K., Review on Melt Cast Explosives, Propellants Explos. Pyrotech., 2011, 36, 393-403.
- [2] Wang J., Li J.S., Huamg Y.G., Dong H.S., A Novel High Energy Density Material Compound 3,4-bis(nitrofurazano)furoxan: Synthesis, Characterization and Properties, New Trends Res. Energ. Mater., Proc. Semin., 11th, Pardubice, 2008, 182-193.
- [3] Feng-qi Z., Pei C., Rong-zu H., Yang L., Zhi-zhong Z., Yan-shui Z., Xu-wu Y., Yin G., Sheng-li G., Qi-zhen S., Thermochemical Properties and Non-Isothermal Decomposition Reaction of 3,4-Dinitrofurazanfuroxan (DNFF), J. Hazard. Mater., 2004, A113, 67-71.
- [4] Zheng W., Wang J., Review on 3,4-Bisnitrofurazanfuroxan (DNTF), Chin. J. Energet. Mat., 2006, 14(6), 463-466, (in Chinese).
- [5] Wang Q., Properties of DNTF-Based Melt-Cast Explosives, Chin. J. Expl. Propell., 2003, 3, 57-59. (in Chinese).
- [6] Ren X., Heng S., Shao Y., Liu Z., Znag G., Wang X., Han F., The Binary Phase Diagram and Eutectic System for DNTF/PETN, Chin. J. Energ. Mater., 2009, 17(4), 455-458 (in Chinese).
- [7] Liu Y., Liu Z., Yin C., The Phase Diagram and Eutectic Binary Systems for 1,3,3-Trinitroazetidine (TNAZ) with some Energetic Materials, Chin. J. Energ. Mater., 2004, 12, 227-230 (in Chinese).
- [8] Hui S.Y., Ning R.X., Ru L.Z., Xiang Z., Ternary Phase Diagrammes of DNTF and TNAZ and Their Eutectics, J. Therm. Anal. Calom., 2010, 103(2), 617-623.
- [9] Zhao S., Dai Z., Zhang C., Li X., The Effect of DNTF and its Eutectics on the Mouldability of PBX, Chin. J. Expl. Propell., 2006, 29(3), 39-42 (in Chinese).
- [10] Wang H., Huang W., Luo Y., Wang H., Shock Sensitivity of DNTF Reduced by Using DNAN, Chin. J. Energ. Mater., 2010, 18(4), 435-438 (in Chinese).
- [11] Astrat′ev A.A., Dashko D.V., Stepanov A.I., Some Peculiarities in Interaction of 3,4-Bis(3-nitrofurazan-4-yl)furoxan with Nucleophilic Agents, Vestnik Kazanskogo Gosudarstvennogo Technologicheskogo Universiteta, 2001, 21, 35-44 (in Russian).
- [12] Astrat′ev A.A., Dashko D.V., Stepanov A.I., Unusual Reaction of 3,4-Bis(3-nitrofurazan-4-yl)furoxan with Ammonia, Primary Amines and Hydrazine, Cent. Eur. J. Chem., 2012, 10(4),1087-1094.
- [13] Stepanov A.I., Astrat′ev A.A., Dashco D.V., Spiridonova N.P., Melnikova S.F., Tzelinsky I.V. Synthesis of Linear and Cyclic Compounds with 3,4-Bis(furazan-3-yl)furoxan Moiety, Izv. Akad. Nauk, Ser. Khim., 2012, 5, 1019-1034 (in Russian).
- [14] Sheremetev A.B., Andrianov V.G., Manttseva E.V., Shatunova E.V., Aleksandrova N.S., Yudin I.L., Dmitriev D.E., Averkiev B.B., Antipin M.Y., Synthesis of Secondary and Tertiary Aminofurazans, Izv. Akad. Nauk, Ser. Khim., 2004, 3, 569-586 (in Russian); Russ. Chem. Bull., Int. Ed., 2004, 53(3), 596-614 (Engl. Transl.).
- [15] Tselinskii I.V., Mel′nikova S.F., Romanova T.V., Spiridonova N.P., Dundukova E.A., Dimerization of Nitrile Oxides of the 1,2,5-Oxadiazole Series. В., Zhurn. Org. Chim. 2001, 37, 1419-1420 (in Russian); Russ. J. Org. Chem., 2001, 37, 1355-1356 (Engl. Transl.).
- [16] Yanshui Z., Bozhou W., Cheng Z., Jiankang L., Zhiqun C., Peng L., Zhizhong Z., Synthesis, Characterization and Crystal Structure Study on 3,4-Bis(4′-azidofurazano-3′-yl)furoxan, Chin. J. Org. Chem., 2010, 30, 1044-1050 (in Chinese).
- [17] Zhou Y., Zhang Z., Li J., Guan X., Huang X., Zhou C., Crystal Structure of 3,4-Dinitrofurazanofuroxan, Chin. J. Expl. Prop., 2005, 28(2), 43-46 (in Chinese).
- [18] Sheremetev A.B., Ivanova E.A., Spiridonova N.P., Melnikova S.F., Tselinsky I.V., Suponitsky K.Y, Antipin M.Y., Desilative Nitration of C,N-Disilated 3-Amino-4-methylfurazan., J. Heterocycl. Chem., 2005, 42, 1237-1242.
- [19] Wang J., Li J., Liang Q., Huang Y., Dong H., A Novel Insensitive High Explosive 3,4-Bis(Aminofurazano)Furoxan, Propellants Explos. Pyrotech., 2008, 33, 347-352.
- [20] Energetic Condensed Systems, (Zhukov B.P., Janus K., Eds.), Moscow, 2nd ed., 2000 (in Russian).
- [21] Sheremetev A.B., Yudin I.L., Advances in Chemistry of Furazano[3,4-b]pyrazines and Their Analogues, Usp. Chim., 2003, 72(1), 93-107 (in Russian); Russ. Chem. Rev., 2003, 72(1), 87-100 (Engl. Transl.).
- [22] Sheremetev A.B., Yudin I.L., Unusual Oxidation of 4-Amino-4H,8H-bisfurazano-[3,4-b:3 ′, 4 ′-e]pyrazines, Mendeleev Commun., 2002, 12(2), 66-67.
- [23] Tselinskii I.V., Mel′nikova S.F., Romanova T.V., Pirogov S.V., Khisamutdinov G.Kh., Mratkhuzina T.A., Korolev V.L., Kondyukov I.Z., Abdrakhmanov I.Sh., Smirnov S.P., 4H,8H-Difurazano[3,4-b:3′,4′-e]pyrazine and Some Its Derivatives, Russ. J. Org. Chem., 1997, 33(11), 1656-1665.
- [24] Starchenkov I.B., Andrianov V.G., Mishnev A.F., Chemistry of Furazano[3,4-b] Pyrazine. 1. Synthesis and Thermodynamic Appraisal of 4,8-Dihydrodifurazano[3,4-b,e]pyrazine and Its Derivatives, Khim. Geterotsikl. Soed., 1997, (2), 250-264 (in Russian); Chem. Heterocycl. Comp., 1997, 33(2), 216-228 (Engl. Transl.).
- [25] Sheremetev A.B., Kharitonova O.V., Mel′nikova T.M., Novikova T.S., Kuz′min V.S., Khmel′nitskii L.I., Synthesis of Symmetrical Difurazanyl Ethers, Mendeleev Commun., 1999, 6(4), 141-143.
- [26] Zhou Y., Wang B., Wang X., Zhou C., Huo H., Zhang Y., Synthesis of Bifurazano[3,4-b:3′4-f]furoxano[3″,4″-d]oxacycloheptatriene, Chin. J. Energ. Mater., 2012, 20(1), 137-138 (in Chinese).
- [27] Zhou Y., Wang B., Xu K., 4,9,12,15-Tetraoxa-3,5,8,10,14,16-hexaazatetracyclo-[11.3.0.02,6.07,11]hexadeca-1(16),2,5,7,10,13-hexaen-3-ium-3-olate monohydrate, Acta Cryst., Structure Reports Online, 2012, E68, o869 doi:10.1107/S160053681200774X
- [28] Khmel′nitskii L.I., Novikov S.S., Godovikova T.I., The Chemistry of Furoxanes: Reactions and Applications, Nauka, Moscow, 1996 (in Russian).
- [29] Pagoria P., Zhang M., DeHope A., Lee G., Mitchell A., Leonard P., ‘Green’ Energetic Materials Synthesis at LLNL, New Trends Res. Energ. Mater., Proc Semin., 15th, Pardubice, 2012, 54-64.
- [30] Sinditskii V.P., Burzhava A.V.,Sheremetev A.B., Aleksandrova N.S., Thermal and Combustion Properties of 3,4-Bis(3-nitrofurazan-4-yl)furoxan (DNTF), Propellants Explos. Pyrotech., 2012, 37, 575-580.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BAT1-0043-0035