Reactions of trifluoromethyl-substituted arylacetylenes with arenes in superacids

被引：0
|
作者：
H. M. H. Alkhafaji
D. S. Ryabukhin
V. M. Muzalevskiy
L. V. Osetrova
A. V. Vasilyev
V. G. Nenajdenko
机构：
[1] St. Petersburg State Forest Technical University,
[2] Moscow State University,undefined
[3] Research Institute for Synthetic Rubber,undefined
[4] St. Petersburg State University,undefined
来源：
Russian Journal of Organic Chemistry | 2013年 / 49卷
关键词：
MeCN; Anisole; Isomer Mixture; MeONa; Isomeric Alkene;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
Protonation of the C≡C bond in trifluoromethyl-substituted arylacetylenes ArC≡CCF3 by the action of superacids (CF3SO3H or HSO3F) generates vinyl cations ArC+=CHCF3 which react with arenes Ar′H to give alkenes Ar(Ar′)C=CHCF3. Protonation of the latter at the C=C bond in the reaction medium yields stable cations Ar(Ar′)C+-CH2CF3 which are converted into E/Z-isomeric alkenes Ar(Ar′)C=CHCF3 and/or alcohols Ar(Ar′)C(OH)CH2CF3 as a result of quenching of superacid reaction solution.
引用
收藏
页码：327 / 341
页数：14
相关论文
共 50 条
  • [11] Trifluoromethyl-Substituted Conjugated Oligoelectrolytes
    Ren, Yan
    Bazan, Guillermo C.
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (36) : 11028 - 11036
  • [12] Linear-selective hydroarylation of unactivated terminal and internal olefins with trifluoromethyl-substituted arenes
    Hartwig, John F. (jhartwig@berkeley.edu), 1600, American Chemical Society (136):
  • [13] TRIFLUOROMETHYL-SUBSTITUTED FLUOROPHOSPHATES AND FLUOROARSENATES
    CHAN, SS
    WILLIS, CJ
    CANADIAN JOURNAL OF CHEMISTRY, 1968, 46 (08): : 1237 - &
  • [14] SYNTHESIS OF TRIFLUOROMETHYL-SUBSTITUTED PYRETHROIDS
    NAGELE, UM
    HANACK, M
    LIEBIGS ANNALEN DER CHEMIE, 1989, (09): : 847 - 852
  • [15] A synthesis of trifluoromethyl-substituted naphthalenes
    Mellor, JM
    El-Sagheer, AH
    Salem, EEDM
    TETRAHEDRON LETTERS, 2000, 41 (38) : 7383 - 7386
  • [16] Linear-Selective Hydroarylation of Unactivated Terminal and Internal Olefins with Trifluoromethyl-Substituted Arenes
    Bair, Joseph S.
    Schramm, York
    Sergeev, Alexey G.
    Clot, Eric
    Eisenstein, Odile
    Hartwig, John F.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (38) : 13098 - 13101
  • [17] CYCLOADDITIONS WITH TRIFLUOROMETHYL-SUBSTITUTED NITRILE YLIDES - INTERCEPTION REACTIONS WITH ENOL ETHERS
    BURGER, K
    EINHELLI.K
    ROTH, WD
    HATZELMA.L
    TETRAHEDRON LETTERS, 1974, (31) : 2701 - 2704
  • [18] REACTIONS OF FLUOROCARBON RADICALS .7. ADDITION TO TRIFLUOROMETHYL-SUBSTITUTED ACETYLENES
    HASZELDINE, RN
    JOURNAL OF THE CHEMICAL SOCIETY, 1952, (SEP): : 3490 - 3498
  • [19] Synthesis and Reactions of Trifluoromethyl-Substituted 1,3,5-Triazines
    Jeon, Woohyung
    Baiazitov, Ramil
    Chierchia, Matteo
    Niederer, Kyle
    Ren, Hongyu
    Moon, Young-Choon
    Gilbert, Bradley B.
    HELVETICA CHIMICA ACTA, 2023, 106 (09)
  • [20] Phototransposition reactions of methyl-substituted benzotrifluorides: Proof of the role of trifluoromethyl-substituted carbon
    DeCosta, D
    Pincock, J
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (26): : 9484 - 9487
12345