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Volumn 47, Issue 33, 2008, Pages 6236-6239

Energetic nitrogen-rich derivatives of 1,5-diaminotetrazole

Author keywords

Azides; Cyclization; Energetic materials; Nitrogen heterocycles

Indexed keywords

AZIDES; CYCLIZATION; ENERGETIC MATERIALS; NITROGEN HETEROCYCLES;

EID: 53549121149     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200801886     Document Type: Article
Times cited : (157)

References (34)
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    • Ed, T. M. Klapötke, Springer, Berlin
    • d) T. M. Klapötke in High Energy Density Materials (Ed.: T. M. Klapötke), Springer, Berlin, 2007, pp. 85-122;
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    • Angew. Chem. Int. Ed. 2007, 46, 1168-1171.
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 1168-1171
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    • b) A. Hantzsch, Chem. Ber. 1933, 66, 1349-1354.
    • (1933) Chem. Ber , vol.66 , pp. 1349-1354
    • Hantzsch, A.1
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    • Preparation of cyanogen azide was based on a modified literature method.[7,8a] At 0°C, cyanogen bromide (1.30 g, 12.3 mmol) was dissolved in dry acetonitrile (20 mL) and sodium azide (3.82 g, 58.8 mmol) was added. The reaction mixture was stirred at 0-15°C for 4 h. The inorganic salt was filtered off (Caution! After filtering, the salt must be quickly dissolved in cold water, The solution was added to a suspension containing 3,6-dihydrazinyl-1,2,4,5-tetrazine[10b, 100 mg (0.704 mmol) in water (10 mL) at 0°C. After 4 d[10c] of stirring at ambient temperature, the suspension was filtered to leave an orange filter cake, which was dried in air. Compound 13 was obtained (127 mg, 0.457 mmol, 65, a) The unknown salt which is formed is likely the azidotetrazolate salt, 7
    • [7]
  • 23
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    • Synthesis of 3,6-dihydrazinyl-1,2,4,5-tetrazine: D. E. Chavez, M. A. Hiskey, J. Heterocycl. Chem. 1998, 35, 1329-1332.
    • b) Synthesis of 3,6-dihydrazinyl-1,2,4,5-tetrazine: D. E. Chavez, M. A. Hiskey, J. Heterocycl. Chem. 1998, 35, 1329-1332.
  • 24
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    • Each compound required a different reaction time (1: 4 h, 6: 2 h, 7: 2 h, 8: 24 h, 9: 3 d, 10: 2 d, 11: 4 d, 12: 24 h, 13: 4 d).
    • c) Each compound required a different reaction time (1: 4 h, 6: 2 h, 7: 2 h, 8: 24 h, 9: 3 d, 10: 2 d, 11: 4 d, 12: 24 h, 13: 4 d).
  • 25
    • 53549085014 scopus 로고    scopus 로고
    • Crystallographic data: 8: (C2H6N 8O, Mr, 158.15; crystal size 0.28 x 0.25 x 0.13 mm; monoclinic, space group Cc, a, 11.2323(7, b, 4.6153(3, c, 11.9898(7) Å, β, 91.413(1)°, V, 621.37(7) Å3, Z, 4, 2θmax, 58°, 829 independent reflections, R1, 0.0281 for 814 reflections with I > 2σ(I) and wR2, 0.0766, 100 parameters. 13: (C12H30N16O 4S4, Mr, 590.76; crystal size 0.44 x 0.23 x 0.14 mm; triclinic, space group P1, a, 8.6351(5, b, 9.0007(5, c, 9.5097(6) Å, α, 92.8441(8, β, 111.4645(7, γ, 103.7774(8)°, V, 660.37(7) Å3, Z, 1, 2θmax, 52°, 2606 independent reflections, R1
    • 2 = 0.0747, 179 parameters. CCDC-684330 and CCDC-684331 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data_request/cif.
  • 32
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    • Gaussian03 (RevisionD.01): M. J. Frisch et al., see Supporting Information.
    • Gaussian03 (RevisionD.01): M. J. Frisch et al., see Supporting Information.
  • 34
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    • Classification of impact sensitivities from reference [5] (insensitive: > 40 J; less sensitive: ≥ 35 J; sensitive: ≥ 4 J; very sensitive: ≤ 3 J).
    • Classification of impact sensitivities from reference [5] (insensitive: > 40 J; less sensitive: ≥ 35 J; sensitive: ≥ 4 J; very sensitive: ≤ 3 J).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.