TiCl4-Et2AlCl-Catalyzed cycloaddition of 1,2-dienes to 1,3,5-cycloheptatriene

被引:12
|
作者
D'yakonov, V. A. [1 ]
Kadikova, G. N. [1 ]
Khalilov, L. M. [1 ]
Dzhemilev, U. M. [1 ]
机构
[1] Russian Acad Sci, Inst Petrochem & Catalysis, Ufa 450075, Russia
基金
俄罗斯基础研究基金会;
关键词
cycloheptatriene; metal complex catalysis; 1,2-dienes; bicyclo[4.2.1]nonanes; allenes; cycloaddition; REARRANGEMENT PATHWAYS; RING-SYSTEM; CYCLOHEPTATRIENE; ALLENES;
D O I
10.1007/s11172-011-0077-z
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A reaction of 1,3,5-cycloheptatriene with 1,2-dienes in the presence of the two-component catalytic system TiCl4-Et2AlCl leads to regio- (similar to 99%) and stereoselective (> 85%) formation of substituted endo-bicyclo[4.2.1]nona-2,4-dienes in up to 80% yields.
引用
收藏
页码:499 / 502
页数:4
相关论文
共 50 条
  • [1] [6π+2π]-Cycloaddition of α,ω-Diallenes and α,ω-Diacetylenes to 1,3,5-Cycloheptatriene in the Presence of TiCl4-Et2AlCl
    D'yakonov, V. A.
    Kadikova, G. N.
    Khalilov, L. M.
    Dzhemilev, U. M.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 49 (08) : 1139 - 1142
  • [2] [6π+2π]-Cycloaddition of α,ω-Diallenes and α,ω-Diacetylenes to 1,3,5-Cycloheptatriene in the Presence of TiCl4-Et2AlCl
    V. A. D’yakonov
    G. N. Kadikova
    L. M. Khalilov
    U. M. Dzhemilev
    Russian Journal of Organic Chemistry, 2013, 49 : 1139 - 1142
  • [3] Regioselective [6π+2π] cycloaddition of 1,2-dienes to 7-substituted 1,3,5-cycloheptatrienes catalyzed by Ti(acac)2Cl2-Et2AlCl
    Kadikova, G. N.
    Kolokoltsev, D. I.
    Meshcheryakova, E. S.
    D'Yakonov, V. A.
    Dzhemilev, U. M.
    RUSSIAN CHEMICAL BULLETIN, 2016, 65 (01) : 195 - 199
  • [4] Regioselective [6π+2π] cycloaddition of 1,2-dienes to 7-substituted 1,3,5-cycloheptatrienes catalyzed by Ti(acac)2Cl2—Et2AlCl
    G. N. Kadikova
    D. I. Kolokoltsev
    E. S. Meshcheryakova
    V. A. D’yakonov
    U. M. Dzhemilev
    Russian Chemical Bulletin, 2016, 65 : 195 - 199
  • [5] SYNTHESIS OF 1-(2,2-DICYANOVINYL)-1,3,5-CYCLOHEPTATRIENE, 1-(2,4,4-TRICYANO-1,3-BUTADIENYL)-1,3,5-CYCLOHEPTATRIENE, 1,6-BIS(2,2-DICYANOVINYL)-1,3,5-CYCLOHEPTATRIENE AND THEIR VINYLOGS
    HIGUCHI, H
    KONDO, M
    YONEHARA, H
    OJIMA, J
    IYODA, M
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1993, 66 (01) : 275 - 281
  • [6] Ti-catalyzed [6π+2π] cycloadditions of allenes with 1,3,5-cycloheptatriene
    D'yakonov, Vladimir A.
    Kadikova, Gulnara N.
    Dzhemilev, Usein M.
    TETRAHEDRON LETTERS, 2011, 52 (21) : 2780 - 2782
  • [7] MICROWAVE SPECTRUM OF 1,3,5-CYCLOHEPTATRIENE
    BUTCHER, SS
    JOURNAL OF CHEMICAL PHYSICS, 1965, 42 (05): : 1833 - &
  • [8] TITANIUM-CATALYZED CYCLOADDITION REACTIONS OF PHENYL(TRIMETHYLSILYL)ACETYLENE TO CONJUGATED DIENES AND 1,3,5-CYCLOHEPTATRIENE - 1-PHENYL-2-(TRIMETHYLSILYL)-CYCLOHEXA-1,4-DIENES AND THEIR AROMATIZATION
    KLEIN, R
    SEDMERA, P
    CEJKA, J
    MACH, K
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1992, 436 (02) : 143 - 153
  • [9] Cyanoesterification of 1,2-Dienes Catalyzed by Nickel
    Hirata, Yasuhiro
    Inui, Tomohiko
    Nakao, Yoshiaki
    Hiyama, Tamejiro
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (18) : 6624 - 6631
  • [10] EXCITED ELECTRONIC STATES OF 1,3,5-CYCLOHEPTATRIENE
    FRUEHOLZ, RP
    RIANDA, R
    KUPPERMANN, A
    CHEMICAL PHYSICS LETTERS, 1978, 55 (01) : 88 - 91