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Synthesis and Diels-Alder reactions of α-fluoro- and α-trifluoromethylacrylonitriles |
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| Authors: | Valentine G Nenajdenko Vasiliy M Muzalevskiy Elizabeth S Balenkova |
| Institution: | a Moscow State University, Department of Chemistry, Leninskie Gory, Moscow 119992, Russia b Institute of Problems of Chemical Physics, Chernogolovka, Moscow Region 142432, Russia c Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, D-48149 Münster, Germany |
| Abstract: | A novel synthetic method for the preparation of α-fluoro- and the still unknown α-trifluoromethylacrylonitriles is elaborated. The reaction of α-fluorovinylbromides and α-trifluoromethylvinylbromides with CuCN leads to the title compounds in good to high yields. While the α-fluoroacrylonitriles were isolated as mixture of Z/E-isomers, the α-trifluoromethylacrylonitriles were obtained as pure Z-isomers. The α-trifluoromethylacrylonitriles are shown to be excellent dienophiles for Diels-Alder reactions. |
| Keywords: | Catalytic olefination reaction Substitution with CuCN α-Fluoroacrylonitriles α-Trifluoromethylacrylonitriles Diels-Alder reaction |
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