Synthesis of 5-amino-6-nitro-1,2,3,4-tetrazine 1,3-dioxide

被引：12
作者：
Guskov, A. A. [1 ]
Klenov, M. S. [1 ]
Churakov, A. M. [1 ]
Tartakovsky, V. A. [1 ]
机构：
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninsky Prosp, Moscow 119991, Russia
来源：
RUSSIAN CHEMICAL BULLETIN | 2016年 / 65卷 / 11期
基金：
俄罗斯科学基金会;
关键词：
1,2,3,4-tetrazine 1,3-dioxides; electrophilic substitution; energetic compounds; C-13 and N-14 NMR spectroscopy; ISO-DTTO; DESIGN;
D O I：
10.1007/s11172-016-1650-2
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
5-Amino-(tert-butyl-NNO-azoxy)-1,2,3,4-tetrazine 1,3-dioxide reacts with nitronium tetra-fluoroborate to give 5-amino-6-nitro-1,2,3,4-tetrazine 1,3-dioxide. This compound is of interest as a new energetic material. A plausible reaction mechanism involves electrophilic substitution of the tert-butyl-NNO-azoxy group by the nitro group.
引用
收藏
页码：2763 / 2765
页数：3
相关论文
共 22 条
  • [1] Are DTTO and iso-DTTO Worthwhile Targets for Synthesis?
    Christe, Karl O.
    Dixon, David A.
    Vasiliu, Monica
    Wagner, Ross I.
    Haiges, Ralf
    Boatz, Jerry A.
    Ammon, Herman L.
    [J]. PROPELLANTS EXPLOSIVES PYROTECHNICS, 2015, 40 (04) : 463 - 468
  • [2] The First Synthesis of 1,2,3,4-Tetrazine-1,3-di-N-oxides
    Churakov, Aleksandr M.
    Ioffe, Sema L.
    Tartakovskii, Vladimir A.
    [J]. MENDELEEV COMMUNICATIONS, 1991, 1 (03) : 101 - +
  • [3] Progress in 1,2,3,4-tetrazine chemistry
    Churakov, AM
    Tartakovsky, VA
    [J]. CHEMICAL REVIEWS, 2004, 104 (05) : 2601 - 2616
  • [4] CHURAKOV AM, 1995, MENDELEEV COMMUN, P227
  • [5] Electrophilic substitution of the tert-butyl-NNO-azoxy group by the bromine atom
    Frumkin, AE
    Churakov, AM
    Tartakovsky, VA
    [J]. RUSSIAN CHEMICAL BULLETIN, 1999, 48 (11) : 2108 - 2111
  • [6] Synthesis of 1,2,3,4-tetrazino[5,6-f]benzo 1,2,3,4-tetrazine 1,3,7,9-tetra-N-oxides
    Frumkin, AE
    Churakov, AM
    Strelenko, YA
    Kachala, VV
    Tartakovsky, VA
    [J]. ORGANIC LETTERS, 1999, 1 (05) : 721 - 724
  • [7] Highly energetic nitrogen species: Reliable energetics via the correlation consistent Composite Approach (ccCA)
    Jorgensen, Kameron R.
    Oyedepo, Gbenga A.
    Wilson, Angela K.
    [J]. JOURNAL OF HAZARDOUS MATERIALS, 2011, 186 (01) : 583 - 589
  • [8] Klenov M. S., 2016, ANGEW CHEM, V38, P11472
  • [9] Toward the Synthesis of Tetrazino-tetrazine 1,3,6,8-Tetraoxide (TTTO): An Approach to Non-annulated 1,2,3,4-Tetrazine 1,3-Dioxides
    Klenov, Michael S.
    Anikin, Oleg V.
    Churakov, Aleksandr M.
    Strelenko, Yurii A.
    Fedyanin, Ivan V.
    Ananyev, Ivan V.
    Tartakovsky, Vladimir A.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (28) : 6170 - 6179
  • [10] Ozonation of benzotetrazine 1,3-dioxides. Facile synthesis of di(methoxycarbonyl)-1,2,3,4-tetrazine 1,3-dioxide
    Klenov, Michael S.
    Churakov, Aleksandr M.
    Strelenko, Yurii A.
    Ananyev, Ivan V.
    Lyssenko, Konstantin A.
    Tartakovsky, Vladimir A.
    [J]. TETRAHEDRON LETTERS, 2015, 56 (40) : 5437 - 5440
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