메뉴 건너뛰기




Volumn 34, Issue 5, 2009, Pages 444-451

Derivatives of 1,1-Diamino-2,2-dinitroethene (DADNE) and Specific reactivity understanding

Author keywords

Amidine; Chlorination; Electrophilic reactions; Nitro ethylenic compounds; Oxidations; Peracid; Tetrazine; Tetrazole

Indexed keywords

AMIDINE; ELECTROPHILIC REACTIONS; NITRO ETHYLENIC COMPOUNDS; PERACID; TETRAZINE; TETRAZOLE;

EID: 70350223983     PISSN: 07213115     EISSN: 15214087     Source Type: Journal    
DOI: 10.1002/prep.200800035     Document Type: Article
Times cited : (28)

References (47)
  • 2
    • 85034262380 scopus 로고    scopus 로고
    • Zöstmark, FOX-7 - A novel, high performance, low vulnerability high explosive for warhead applications
    • Orlando, Florida, September 23 - 27
    • B. Janzon, H. Bergman, C. Eldstäter, Lamnvik, H. ZÖstmark,FOX-7 - A Novel, High Performance, Low Vulnerability High Explosive for Warhead Applications, 20th International Symposium on Ballistics, Orlando, Florida, September 23 - 27, 2002, pp. 686 - 693.
    • (2002) 20th International Symposium on Ballistics , pp. 686
    • Janzon, B.1    Bergman, H.2    Eldstäter, C.3    Lamnvik, H.4
  • 3
    • 0003394112 scopus 로고    scopus 로고
    • d) were based on the calculated values of density [3b] and heat of formation [3c]. Quantum mechanical calculations were used to theoretically optimize the geometry of the unknown molecules to estimate the density and the heat of formation. A hybrid method between Density Functional Theory (DFT) and Hartree-Fock approximation (HF) called B3LYP was used for that purpose. The basis set used was 6-31G(d)
    • d) were based on the calculated values of density [3b] and heat of formation [3c]. Quantum mechanical calculations were used to theoretically optimize the geometry of the unknown molecules to estimate the density and the heat of formation. A hybrid method between Density Functional Theory (DFT) and Hartree-Fock approximation (HF) called B3LYP was used for that purpose. The basis set used was 6-31G(d)
    • Cheetah 2.0
    • Fried, L.1    Howard, W.M.2    Souers, P.C.3
  • 4
    • 84912123059 scopus 로고
    • Prediction of possible crystal structures for C-, H-, N-, O-, and F-containing organic compounds
    • b) The densities were calculated with the program MOLPACK (MOLecular PAcKing) from the university of Maryland, see for more details: J. R. Holden, Z. Du, H. L. Ammon, Prediction of Possible Crystal Structures for C-, H-, N-, O-, and F-Containing Organic Compounds, J. Comput. Chem. 1993, 14, 422;
    • (1993) J. Comput. Chem. , vol.14 , pp. 422
    • Holden, J.R.1    Du, Z.2    Ammon, H.L.3
  • 5
    • 84986464710 scopus 로고
    • Nonlocal density functional calculation of gas phase heats of formation
    • c) The heat of formation in the gas phase was determined with the use of density functional theory with B3LYP parameterization. To calculate the solid state heat of formation it is necessary to subtract the sublimation enthalpy (determined by program MOLPACK) from that of gas phase. This approach is based on the scheme of Habibollahzadeh et al.: D. Habibollahzadeh, M. E. Grice, M. C. Concha, J. S. Murray, P. Politzer, Nonlocal Density Functional Calculation of Gas Phase Heats of Formation, J. Comput. Chem. 1995, 16, 654.
    • (1995) J. Comput. Chem. , vol.16 , pp. 654
    • Habibollahzadeh, D.1    Grice, M.E.2    Concha, M.C.3    Murray, J.S.4    Politzer, P.5
  • 7
    • 0001756526 scopus 로고    scopus 로고
    • 1,1-diamino-2,2-dinitroethylene: A novel energetic material with infinite layers in two dimensions
    • U. Bemm, H. Östmark, 1,1-Diamino-2,2-dinitroethylene: A Novel Energetic Material with Infinite Layers in Two Dimensions, Acta Cryst. 1998, C54, 1997.
    • (1998) Acta Cryst. , vol.C54
    • Bemm, U.1    Östmark, H.2
  • 8
    • 0036345567 scopus 로고    scopus 로고
    • Transamination reactions of 1,1-diamino-2,2-dinitroethene (FOX-7)
    • The only mechanistic aspect mentioned in the literature about the "push-pull" effect was given by: A. J. Bellamy, N. V. Latypov, P. Goede, Transamination Reactions of 1,1-Diamino-2,2-dinitroethene (FOX-7), J. Chem. Res. (M) 2002, 641.
    • (2002) J. Chem. Res. (M) , vol.641
    • Bellamy, A.J.1    Latypov, N.V.2    Goede, P.3
  • 9
    • 34250370030 scopus 로고    scopus 로고
    • FOX-7 (1,1-diamino-2,2-dinitroethene)
    • T. M. Klapötke (Ed.) , Springer-Verlag textbook series on Structure and Bonding, Berlin
    • See also a recent review: A. J. Bellamy, FOX-7 (1,1-Diamino-2,2- dinitroethene), in: T. M. Klapötke (Ed.), High Energy Density Material, Vol. 125, Springer-Verlag textbook series on Structure and Bonding, Berlin 2007, pp. 1 - 33.
    • (2007) High Energy Density Material , vol.125 , pp. 1
    • Bellamy, A.J.1
  • 10
    • 33746535068 scopus 로고    scopus 로고
    • α- and β-FOX-7, polymorphs of a high energy density material, studied by X-ray single crystal and powder investigations in the temperature range from 200 to 423 K
    • J. Evers, T. M. Klapötke, P. Mayer, G. Oehlinger, J. M. Welch, α- and β-FOX-7, Polymorphs of a High Energy Density Material, Studied by X-ray Single Crystal and Powder Investigations in the Temperature Range from 200 to 423 K, Inorg. Chem. 2006, 45, 4996.
    • (2006) Inorg. Chem. , vol.45 , pp. 4996
    • Evers, J.1    Klapötke, T.M.2    Mayer, P.3    Oehlinger, G.4    Welch, J.M.5
  • 12
    • 0342408236 scopus 로고
    • Oxydations des Amines Aromatiques Primaires
    • For an exhaustive review of oxidants, see: M. Hedayatullah, Oxydations des Amines Aromatiques Primaires, Bull. Soc. Chim. Fr. 1972, 2957.
    • (1972) Bull. Soc. Chim. Fr. , pp. 2957
    • Hedayatullah, M.1
  • 14
    • 1642491873 scopus 로고    scopus 로고
    • Synthesis of 3-azido-5-amino-1,2,4-triazole
    • b) T. P. Kofman, V. I. Namestnikov, Synthesis of 3-azido-5-amino-1,2,4- triazole, Russ. J. Org. Chem. 2003, 39, 579.
    • (2003) Russ. J. Org. Chem. , vol.39 , pp. 579
    • Kofman, T.P.1    Namestnikov, V.I.2
  • 15
    • 37049156095 scopus 로고
    • Oxidations with lead tetra-acetate. Part II. the oxidation of primary aromatic amines
    • a) K. H. Pausacker, J. G. Scroggie, Oxidations with Lead Tetra-Acetate. Part II. The Oxidation of Primary Aromatic Amines, J. Chem. Soc. 1954, 4003;
    • (1954) J. Chem. Soc. , pp. 4003
    • Pausacker, K.H.1    Scroggie, J.G.2
  • 16
    • 0000280097 scopus 로고
    • Formation of symmetric azo-compounds from primary aromatic amines by lead tetraacetate
    • b) E. Baer, A. L. Tasoni, Formation of Symmetric Azo-Compounds from Primary Aromatic Amines by Lead Tetraacetate, J. Am. Chem. Soc. 1956, 78, 2857;
    • (1956) J. Am. Chem. Soc. , vol.78 , pp. 2857
    • Baer, E.1    Tasoni, A.L.2
  • 17
    • 84943886801 scopus 로고
    • Neue, durch mesomerie stabilisierte sauerstoffradikale
    • c) K. Dimroth, F. Falk, G. Nebauer, Neue, durch Mesomerie stabilisierte Sauerstoffradikale, Chem. Ber. 1957, 90, 2058.
    • (1957) Chem. Ber. , vol.90 , pp. 2058
    • Dimroth, K.1    Falk, F.2    Nebauer, G.3
  • 18
    • 84979192029 scopus 로고
    • Die Oxydation des Diphenylamins
    • a) H. Wieland, S. Gambarajan, Die Oxydation des Diphenylamins, Chem. Ber. 1906, 39, 1499;
    • (1906) Chem. Ber. , vol.39 , pp. 1499
    • Wieland, H.1    Gambarajan, S.2
  • 20
    • 0347196791 scopus 로고
    • Mechanism of the oxidation of nitrosobenzenes by peroxoacetic acid
    • a) K. M. Ibne-Rasa, G. C. Lauro, Mechanism of the Oxidation of Nitrosobenzenes by Peroxoacetic Acid, J. Am. Chem. Soc. 1963, 85, 1165;
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 1165
    • Ibne-Rasa, K.M.1    Lauro, G.C.2
  • 21
    • 0000330092 scopus 로고
    • Kinetics of the peroxymonophosphoric acid oxidation of aromatic amines
    • b) Y. Ogata, K. Tomizawa, T. Morikawa, Kinetics of the Peroxymonophosphoric Acid Oxidation of Aromatic Amines, J. Org. Chem. 1979, 44, 352;
    • (1979) J. Org. Chem. , vol.44 , pp. 352
    • Ogata, Y.1    Tomizawa, K.2    Morikawa, T.3
  • 22
    • 0036501379 scopus 로고    scopus 로고
    • Zirconium-catalyzed amine oxidation: A mechanistic study
    • c) R. Thiel, K. Krohn, Zirconium-Catalyzed Amine Oxidation: A Mechanistic Study, Chem. Eur. J. 2002, 8, 1049;
    • (2002) Chem. Eur. J. , vol.8 , pp. 1049
    • Thiel, R.1    Krohn, K.2
  • 23
    • 0013608882 scopus 로고
    • 3CN complex made directly from fluorine and water
    • 3CN Complex Made Directly from Fluorine and Water, J. Org. Chem. 1992, 57, 7342;
    • (1992) J. Org. Chem. , vol.57 , pp. 7342
    • Rozen, S.1    Kol, M.2
  • 25
    • 30144437908 scopus 로고
    • Dioxiranes: Synthesis and reactions of methyldioxiranes
    • a) R. W. Murray, R. Jeyaraman, Dioxiranes: Synthesis and Reactions of Methyldioxiranes, J. Org. Chem. 1985, 50, 2847;
    • (1985) J. Org. Chem. , vol.50 , pp. 2847
    • Murray, R.W.1    Jeyaraman, R.2
  • 26
    • 0024796851 scopus 로고
    • Chemistry of dioxiranes. 13. Oxidation of primary amines by dimethyldioxirane
    • b) R.W. Murray, S. N. Rajadhyaksha, L. Mohan, Chemistry of Dioxiranes. 13. Oxidation of Primary Amines by Dimethyldioxirane, J. Org. Chem. 1989, 54, 5783.
    • (1989) J. Org. Chem. , vol.54 , pp. 5783
    • Murray, R.W.1    Rajadhyaksha, S.N.2    Mohan, L.3
  • 27
    • 11144306763 scopus 로고
    • Increasing the index of covalent oxygen bonding at nitrogen attached to carbon
    • For an exhaustive review, see: J. H. Boyer, Increasing the Index of Covalent Oxygen Bonding at Nitrogen Attached to Carbon, Chem. Rev. 1980, 80, 495.
    • (1980) Chem. Rev. , vol.80 , pp. 495
    • Boyer, J.H.1
  • 28
    • 37049052010 scopus 로고
    • Aromatic polyfluoro-compounds. Part XXIII. Polyfluoroazo, -azoxy-, and -hydrazo-benzenes
    • J. Burdon, D. F. Thomas, Aromatic Polyfluoro-Compounds. Part XXIII. Polyfluoroazo, -Azoxy-, and -Hydrazo-benzenes, J. Chem. Soc. 1965, 2621.
    • (1965) J. Chem. Soc. , pp. 2621
    • Burdon, J.1    Thomas, D.F.2
  • 29
    • 0002381467 scopus 로고
    • Chemistry of Dinitroacetonitrile - IV: Preparation and Properties of Esters of Dinitrocyanoacetic Acid
    • a) C. O. Parker, Chemistry of Dinitroacetonitrile - IV: Preparation and Properties of Esters of Dinitrocyanoacetic Acid, Tetrahedron 1962, 17, 109 - 116;
    • (1962) Tetrahedron , vol.17 , pp. 109-116
    • Parker, C.O.1
  • 30
    • 0003035718 scopus 로고
    • Chemistry of dinitroacetonitrile - I: Preparation and properties of dinitroacetonitrile and its salts
    • b) C. O. Parker, H. A. Rolewicz, K. S. McCallum, Chemistry of Dinitroacetonitrile - I: Preparation and Properties of Dinitroacetonitrile and Its Salts, Tetrahedron 1962, 17, 79;
    • (1962) Tetrahedron , vol.17 , pp. 79
    • Parker, C.O.1    Rolewicz, H.A.2    McCallum, K.S.3
  • 31
    • 84904116361 scopus 로고
    • Sur la constitution de l'acide fulminique et une nouvelle série de corps dérivés de l'acide acétique
    • c) The first description of dinitroacetonitrile 5 was reported in 1857: M. L. Chichkoff, Sur la constitution de l'acide fulminique et une nouvelle série de corps dérivés de l'acide acétique, Ann. Chim. (Paris) 1857, 49, 310.
    • (1857) Ann. Chim. (Paris) , vol.49 , pp. 310
  • 32
    • 20444501301 scopus 로고    scopus 로고
    • The reactivity of 1,1-diamino-2,2-dinitroethene (FOX-7)
    • G. Hervé, G. Jacob, N. Latypov, The Reactivity of 1,1-Diamino-2,2-dinitroethene (FOX-7), Tetrahedron 2005, 61, 6743.
    • (2005) Tetrahedron , vol.61 , pp. 6743
    • Hervé, G.1    Jacob, G.2    Latypov, N.3
  • 33
    • 70350227110 scopus 로고    scopus 로고
    • If the same chlorination reaction was carried out with only one equivalent of N-chlorosuccinimide, the resulting product was still the double substituted compound 5 accompanied with unreacted DADNE 1 (see the experimental section). This indicates that the second step of the chlorination is faster than the first one. See Ref [16] for more details.
    • If the same chlorination reaction was carried out with only one equivalent of N-chlorosuccinimide, the resulting product was still the double substituted compound 5 accompanied with unreacted DADNE 1 (see the experimental section). This indicates that the second step of the chlorination is faster than the first one. See Ref [16] for more details.
  • 34
    • 0032566029 scopus 로고    scopus 로고
    • Catalytic friedel - Crafts acylation of benzene, chlorobenzene, and fluorobenzene using a novel catalyst system, hafnium triflate and trifluoromethanesulfonic acid
    • S. Kobayashi, S. Iwamoto, Catalytic Friedel - Crafts Acylation of Benzene, Chlorobenzene, and Fluorobenzene Using a Novel Catalyst System, Hafnium Triflate and Trifluoromethanesulfonic Acid, Tetrahedron Lett. 1998, 39, 4697;
    • (1998) Tetrahedron Lett. , vol.39 , pp. 4697
    • Kobayashi, S.1    Iwamoto, S.2
  • 35
    • 0036625262 scopus 로고    scopus 로고
    • Rare-earth metal triflates in organic synthesis
    • a) For an exhaustive review on Lanthanide triflates, see: S. Kobayashi, M. Sugiura, H. Kitagawa, W.W.-L. Lam, Rare-Earth Metal Triflates in Organic Synthesis, Chem. Rev. 2002, 102, 2227.
    • (2002) Chem. Rev. , vol.102 , pp. 2227
    • Kobayashi, S.1    Sugiura, M.2    Kitagawa, H.3    Lam, W.-L.4
  • 36
    • 0141742409 scopus 로고    scopus 로고
    • New protocol for efficient N-chlorinations of amides and carbamates
    • O. V. Larionov, S. I. Kozhushkov, A. De Meijere, New Protocol for Efficient N-Chlorinations of Amides and Carbamates, Synthesis 2003, 1916.
    • (2003) Synthesis , pp. 1916
    • Larionov, O.V.1    Kozhushkov, S.I.2    De Meijere, A.3
  • 38
    • 84987505934 scopus 로고
    • Dense energetic compounds of C, H, N, and O Atoms IV nitro and azidofurazan derivatives
    • b) A. Gunasekaran, M. L. Trudell, J. H. Boyer, Dense Energetic Compounds of C, H, N, and O Atoms IV Nitro and Azidofurazan Derivatives, Heteroatom. Chem. 1994, 5, 441;
    • (1994) Heteroatom. Chem. , vol.5 , pp. 441
    • Gunasekaran, A.1    Trudell, M.L.2    Boyer, J.H.3
  • 39
    • 84986409403 scopus 로고
    • Dense energetic compounds of C, H, N, and O Atoms. III. 5-[4-Nitro-(1,2,5)oxadiazolyl]-5H-[1,2,3] triazolo[4,5-c][1,2,5]oxadiazole
    • c) A. Gunasekaran, J. H. Boyer, Dense Energetic Compounds of C, H, N, and O Atoms. III. 5-[4-Nitro-(1,2,5)oxadiazolyl]-5H-[1,2,3] triazolo[4,5-c][1,2,5] oxadiazole, Heteroatom. Chem. 1993, 4, 521;
    • (1993) Heteroatom. Chem. , vol.4 , pp. 521
    • Gunasekaran, A.1    Boyer, J.H.2
  • 41
    • 0141922469 scopus 로고
    • Oxidation of aminopyridines to nitropyridines
    • a) R. H. Wiley, J. L. Hartman, Oxidation of Aminopyridines to Nitropyridines, J. Am. Chem. Soc. 1951, 73, 494;
    • (1951) J. Am. Chem. Soc. , vol.73 , pp. 494
    • Wiley, R.H.1    Hartman, J.L.2
  • 42
    • 0004383771 scopus 로고
    • Pyrrolopyridines. IV. Synthesis of possible intermediates
    • b) W. Herz, Pyrrolopyridines. IV. Synthesis of Possible Intermediates, J. Org. Chem. 1961, 26, 122.
    • (1961) J. Org. Chem. , vol.26 , pp. 122
    • Herz, W.1
  • 43
    • 37049059035 scopus 로고
    • Aromatic polyfluoro-compounds. Part VII. the reaction of pentafluoronitrobenzene with ammonia
    • a) G. M. Brooke, J. Burdon, J. C. Tatlow, Aromatic Polyfluoro-Compounds. Part VII. The Reaction of Pentafluoronitrobenzene with Ammonia, J. Chem. Soc. 1961, 802;
    • (1961) J. Chem. Soc. , pp. 802
    • Brooke, G.M.1    Burdon, J.2    Tatlow, J.C.3
  • 44
    • 0009381075 scopus 로고
    • Peroxytrifluoroacetic Acid. II. the oxidation of anilines to nitrobenzenes
    • b)W. D. Emmons, Peroxytrifluoroacetic Acid. II. The Oxidation of Anilines to Nitrobenzenes, J. Am. Chem. Soc. 1954, 76, 3470.
    • (1954) J. Am. Chem. Soc. , vol.76 , pp. 3470
    • Emmons, W.D.1
  • 45
    • 33845382756 scopus 로고    scopus 로고
    • Novel illustrations of the specific reactivity of 1,1-diamino-2,2- dinitroethene (DADNE) leading to new unexpected compounds
    • G. Hervé, G. Jacob, Novel Illustrations of the Specific Reactivity of 1,1-Diamino-2,2-dinitroethene (DADNE) Leading to New Unexpected Compounds, Tetrahedron 2007, 63, 953.
    • (2007) Tetrahedron , vol.63 , pp. 953
    • Hervé, G.1    Jacob, G.2
  • 46
    • 0008646673 scopus 로고
    • Synthesis of polynitro compounds. Peroxydisulfuric acid oxidation of polynitroarylamines to polynitro aromatics
    • A. T. Nielsen, R. L. Atkin, W. P. Norris, C. L. Coon, M. E. Sitzmann, Synthesis of Polynitro Compounds. Peroxydisulfuric Acid Oxidation of Polynitroarylamines to Polynitro Aromatics, J. Org. Chem. 1980, 45, 2341.
    • (1980) J. Org. Chem. , vol.45 , pp. 2341
    • Nielsen, A.T.1    Atkin, R.L.2    Norris, W.P.3    Coon, C.L.4    Sitzmann, M.E.5
  • 47
    • 0347896865 scopus 로고
    • Nitration of 1,1-diamino-2,2-dinitroethylenes
    • K. Baum, N. V. Nguyen, Nitration of 1,1-Diamino-2,2-dinitroethylenes, J. Org. Chem. 1992, 57, 3026.
    • (1992) J. Org. Chem. , vol.57 , pp. 3026
    • Baum, K.1    Nguyen, N.V.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.