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Reactions of trifluoromethyl-substituted arylacetylenes with arenes in superacids |
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| Authors: | H. M. H. Alkhafaji D. S. Ryabukhin V. M. Muzalevskiy L. V. Osetrova A. V. Vasilyev V. G. Nenajdenko |
| Affiliation: | 1257. St. Petersburg State Forest Technical University, Institutskii per. 5, St. Petersburg, 194021, Russia 2257. Moscow State University, Vorob’evy gory 3, Moscow, 119899, Russia 3257. Research Institute for Synthetic Rubber, Gapsal’skaya ul. 1, St. Petersburg, 198035, Russia 4257. St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia |
| Abstract: | 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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