STUDY OF THE BROMINATION OF 1,5-DINITRO-3-AZABICYCLO[3.3.1]NON-6-ENES

被引:0
|
作者
Shakhkeldyan, I. V. [1 ]
Atroshchenko, Yu. M. [1 ]
Melekhina, N. K. [1 ]
Yakunina, I. E. [1 ]
Kobrakov, K. I. [2 ]
Shumsky, A. N. [3 ]
机构
[1] LN Tolstoy Tula State Pedag Univ, Tula 300026, Russia
[2] AN Kosygin Moscow State Text Univ, Moscow 117419, Russia
[3] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 117913, Russia
关键词
3-azabicyclo[3,3,1]non-6-enes; homo- and heteronuclear correlation spectroscopy; halogenation;
D O I
10.1007/s10593-008-0107-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The electrophilic addition of bromine to 3-substituted 1,5-dinitro-3-azabicyclo[3.3.1]non-6-ene in carbon tetrachloride is accompanied by intramolecular 3,7-cyclization with the formation of 6-bromo-3-R-1,5-dinitro-3-azonia-tricyclo[3.3.10(3,7)]nonane tribromides. In the bromination of 1,5-dinitro-3-azabicyclo[3.3.1]non-6-enes containing substituents at the double bond, molecular complexes of halogen with the substrate were obtained.
引用
收藏
页码:690 / 699
页数:10
相关论文
共 50 条
  • [41] Synthesis of N-substituted 9-[2-(3,4-methylenedioxyphenyl)-2-oxoethyl]-1,5- dinitro-7,8-benzo-3-azabicyclo[3.3.1]non-7-en-6-ones
    Yakunina I.E.
    Atroshchenko Yu.M.
    Shahkheldyan I.V.
    Kobrakov K.I.
    Troizkiy N.A.
    Boikova O.I.
    Chem. Heterocycl. Compd., 2007, 9 (1174-1180): : 1174 - 1180
  • [42] The first preparation of (1S,5R)-(-)- and (1R,5S)-(+)-7-phenyl-3-borabicyclo[3.3.1]non-6-enes and their application for synthesis of chiral cyclohexene derivatives
    Gurskii, ME
    Karionova, AL
    Ignatenko, AV
    Lyssenko, KA
    Antipin, MY
    Bubnov, YN
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (11) : 2840 - 2846
  • [43] Synthesis of 7,8-benzo-3-hydroxy-9-azabicyclo[3.3.1]non-3-enes by cyclocondensation of 1,3-bis-silyl enol ethers with isoquinolines
    Schmidt, A
    Gütlein, JP
    Preuss, A
    Albrecht, U
    Reinke, H
    Langer, P
    SYNLETT, 2005, (16) : 2489 - 2491
  • [44] Chemistry of 3-azabicyclo[3.3.1]nonane: II. Reduction of 6-acetoxy-3-benzyl-1-ethoxycarbonyl-3-azabicyclo[3.3.1]nonan-9-one with sodium borohydride
    Vafina, GF
    Yakhina, GR
    Spirikhin, LV
    Galin, FZ
    Yunusov, MS
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 41 (08) : 1208 - 1211
  • [45] Synthesis and Structure of Derivatives of 9-(2-Oxopropyl)-1,5-dinitro-7,8-benzo-3-azabicylo[3.3.1]non-7-en-6-ones
    I. E. Yakunina
    I. V. Shakhkeldyan
    Yu. M. Atroshenko
    O. Ya. Borbulevich
    V. V. Nesterov
    M. B. Kopyshev
    N. A. Troitskii
    Yu. A. Efremov
    E. N. Alifanova
    V. A. Subbotin
    Russian Journal of Organic Chemistry, 2004, 40 : 239 - 246
  • [46] Synthesis and structure of derivatives of 9-(2-oxopropyl)1,5-dinitro-7,8-benzo-3-azabicylo[3.3.1]non-7-en-6-ones
    Yakunina, IE
    Shakhkeldyan, IV
    Atroshenko, YM
    Borbulevich, OY
    Nesterov, VV
    Kopyshev, MB
    Troitskii, NA
    Efremov, YA
    Alifanova, EN
    Subbotin, VA
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 40 (02) : 239 - 246
  • [47] Chemistry of 3-Azabicyclo[3.3.1]nonane: II. Reduction of 6-Acetoxy-3-benzyl-1- ethoxycarbonyl-3-azabicyclo[3.3.1]nonan-9-one with Sodium Borohydride
    G.F. Vafina
    G.R. Yakhina
    L.V. Spirikhin
    F.Z. Galin
    M.S. Yunusov
    Russian Journal of Organic Chemistry, 2005, 41 : 1208 - 1211
  • [48] INCIPIENT NUCLEOPHILIC ADDITIONS .4. 1,5-DINITRO-3-METHYL-3-AZABICYCLO[3,3,1]NONAN-7-ONE
    KAFTORY, M
    DUNITZ, JD
    ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1976, 32 (JAN15): : 1 - 4
  • [49] 1,4-CYCLOHEPTYLENE AND THE RELATED ALLYLIC DIRADICALS - THERMAL NITROGEN EXTRUSION FROM 6,7-DIAZABICYCLO[3.2.2]NON-6-ENES
    UYEHARA, T
    TAKAHASHI, M
    KATO, T
    TETRAHEDRON LETTERS, 1985, 26 (09) : 1241 - 1244
  • [50] SYNTHESIS AND ACIDOLYSIS OF 3-ENDO-AZIDOMETHYL[3.3.1]NON-6-ENE AND "3-ENDO-AZIDOBICYCLO[3.3.1]NON-6-ENE - A NOVEL SYNTHESIS OF 4-AZAHOMOADAMANT-4-ENES
    SASAKI, T
    EGUCHI, S
    TOI, N
    OKANO, T
    FURUKAWA, Y
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (10): : 2529 - 2534