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：
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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.
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页码：327 / 341
页数：14
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