Catalytic epoxidation of 5-vinyl-2-norbornene with organic hydroperoxides

被引:0
|
作者
Osokin, MY [1 ]
Karpov, OP
Kryukov, SI
Surovtsev, AA
Osokin, YG
Bychkov, BN
机构
[1] Yaroslavl State Tech Univ, Yaroslavl, Russia
[2] OAO Yarsintez Res Inst, Yaroslavl, Russia
关键词
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
5-Vinyl-2-norbornene is epoxidized with tert-butyl, tert-amyl, or cumyl hydroperoxide in the presence of molybdenyl ethanediolate at either or both of the double bonds of the hydrocarbon to afford preferentially 2,3-epoxy-5-vinylnorbornane. The reactivity of tert-alkyl hydroperoxides correlates with their structure characterized by the Taft polar substituent constants. The rho* value found to be 1.08 confirms the electrophilic character of the catalytic hydroperoxide epoxidation and indicates a low polarity of the activated complex of the reaction.
引用
收藏
页码:410 / 414
页数:5
相关论文
共 50 条
  • [41] Influence of the Nature of Chemical Modification of Addition Poly(5-vinyl-2-norbornene) on the Gas Permeability of Hydrocarbons
    A. I. Wozniak
    I. L. Borisov
    E. V. Bermesheva
    D. P. Zarezin
    A. V. Volkov
    E. Sh. Finkelstein
    M. V. Bermeshev
    Polymer Science, Series B, 2020, 62 : 218 - 224
  • [42] Making accessible soluble silicon-containing polynorbornenes: hydrosilylation of vinyl-addition poly(5-vinyl-2-norbornene)
    Wozniak, Alyona I.
    Bermesheva, Evgeniya V.
    Borisov, Ilya L.
    Rzhevskiy, Sergey A.
    Tyutyunov, Andrey A.
    Ilyin, Sergey O.
    Topchiy, Maxim A.
    Asachenko, Andrey F.
    Bermeshev, Maxim V.
    POLYMER CHEMISTRY, 2023, 14 (48) : 5274 - 5285
  • [43] Synthesis and Characterization of Low- and High-Molecular-Weight Products Based on 5-vinyl-2-norbornene
    Piskunova, Ekaterina S.
    Shorunov, Sergey V.
    Alentiev, Dmitry A.
    Bermeshev, Maxim V.
    9TH INTERNATIONAL CONFERENCE ON STRUCTURAL ANALYSIS OF ADVANCED MATERIALS (ICSAAM 2019), 2019, 2196
  • [44] Kinetic Model and Mechanism of Heterogeneous Hydrogenation of Strained Polycyclic Compounds Derived from 5-Vinyl-2-norbornene
    V. V. Zamalyutin
    E. A. Katsman
    V. R. Flid
    Petroleum Chemistry, 2023, 63 : 277 - 288
  • [45] Kinetic Model and Mechanism of Heterogeneous Hydrogenation of Strained Polycyclic Compounds Derived from 5-Vinyl-2-norbornene
    Zamalyutin, V. V.
    Katsman, E. A.
    Flid, V. R.
    PETROLEUM CHEMISTRY, 2023, 63 (03) : 277 - 288
  • [46] Highly efficient vinylic addition polymerization of 5-vinyl-2-norbornene using benzylic palladium complexes as precatalysts
    Perez-Ortega, Ignacio
    Albeniz, Ana C.
    POLYMER CHEMISTRY, 2021, 12 (41) : 5963 - 5969
  • [47] HOMOGENEOUS CATALYTIC EPOXIDATION OF OLEFINS WITH ORGANIC HYDROPEROXIDES IN PRESENCE OF MOLYBDENUM CATALYSTS
    FARBEROV, MI
    STOZHKOV.GA
    BONDAREN.AV
    KIRIK, TM
    INTERNATIONAL CHEMICAL ENGINEERING, 1972, 12 (04): : 634 - &
  • [48] A kinetic model of the cycloaddition reactions between cyclopentadiene and 1,3-butadiene for synthesis of 5-vinyl-2-norbornene
    Li, Hao
    Liu, Xue
    Zhang, Yan
    Xiao, Yang
    Cao, Kun
    CANADIAN JOURNAL OF CHEMICAL ENGINEERING, 2024, 102 (05): : 1946 - 1956
  • [49] STUDY OF EPOXIDATION OF BUT-2-ENE WITH ORGANIC HYDROPEROXIDES
    OBUKHOV, VM
    BONDAREN.AV
    FARBEROV, MI
    LYSANOV, VA
    PETROLEUM CHEMISTRY, 1971, 11 (02) : 132 - &
  • [50] POLAROGRAPHY OF UNIVALENT-COPPER COMPLEXES WITH THE ENDO-ISOMER AND EXO-ISOMER OF 5-VINYL-2-NORBORNENE
    KANEVSKAYA, TR
    KANEVSKII, IM
    SOVIET ELECTROCHEMISTRY, 1990, 26 (09): : 1084 - 1087