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
  • [21] A VIBRATIONAL SPECTROSCOPIC INVESTIGATION OF SOLID 1,3,5-CYCLOHEPTATRIENE
    HAINES, J
    GILSON, DFR
    PHASE TRANSITIONS, 1990, 21 (01) : 1 - 9
  • [22] PHOTOADDITIONS OF ANTHRACENES TO 2,4-HEXADIENE AND 1,3,5-CYCLOHEPTATRIENE
    KAUPP, G
    GRUTER, HW
    TEUFEL, E
    CHEMISCHE BERICHTE-RECUEIL, 1983, 116 (02): : 630 - 644
  • [23] Palladium-catalyzed regioselective silaboration of 1,2-dienes
    Suginome, M
    Ohmori, Y
    Ito, Y
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 611 (1-2) : 403 - 413
  • [24] Nickel-catalyzed acylstannylation and alkynylstannylation of 1,2-dienes
    Nakao, Y
    Shirakawa, E
    Tsuchimoto, T
    Hiyama, T
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (23) : 3701 - 3721
  • [25] COOLIGOMERIZATION OF 1,2-DIENES WITH NORBORNADIENES CATALYZED BY COBALT COMPLEXES
    DZHEMILEV, UM
    KHUSNUTDINOV, RI
    MUSLIMOV, ZS
    TOLSTIKOV, GA
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1988, 37 (06): : 1183 - 1191
  • [26] DIELS-ALDER REACTION OF 1,3,5-CYCLOHEPTATRIENE WITH THIOBENZOPHENONE
    OHNISHI, Y
    AKASAKI, Y
    OHNO, A
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1973, 46 (10) : 3307 - 3308
  • [27] Cyclo- and carbomagnesiation of 1,2-dienes catalyzed by Zr complexes
    Dzhemilev, UM
    D'yakonov, VA
    Khafizova, LO
    Ibragimov, AG
    TETRAHEDRON, 2004, 60 (06) : 1287 - 1291
  • [28] Rhodium(I)-catalyzed regioselective additions of chloroformates to 1,2-dienes
    Hua, RM
    Tanaka, M
    TETRAHEDRON LETTERS, 2004, 45 (11) : 2367 - 2370
  • [29] Superbasicity of 1,3,5-cycloheptatriene derivatives and their proton sponges in gas phase
    Valadbeigi, Younes
    CHEMICAL PHYSICS LETTERS, 2017, 689 : 1 - 7
  • [30] The mechanisms for triple gold(I)-catalyzed (4+1) cycloaddition of methylenecyclopropane with 7-naphthyl-1,3,5-cycloheptatriene: Insight into from density functional calculations
    Song, Zhijun
    Liu, Chengcheng
    Chen, Xuelin
    Yan, Wenhui
    Cao, Yifan
    Xie, Hujun
    Lei, Qunfang
    Fang, Wenjun
    COMPUTATIONAL AND THEORETICAL CHEMISTRY, 2016, 1084 : 25 - 35