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Mechanistic study of multi-step nucleophilic substitution for trifluoromethylated styrenes |
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| Authors: | Alexander Yu. Rulev Igor A. Ushakov Evgeniy V. Kondrashov Vasiliy M. Muzalevskiy Aleksey V. Shastin Valentine G. Nenajdenko |
| Affiliation: | aA.E. Favorsky Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1, Favorsky Str., Irkutsk 664033, Russia;bMoscow State University, Department of Chemistry, Leninskie Gory, Moscow 119992, Russia;cInstitute of Problems of Chemical Physics, Chernogolovka, Moscow Region 142432, Russia |
| Abstract: | The key steps of the reactions of nitrogen nucleophiles with β-halogen-β-trifluoromethylstyrenes have been studied by 19F and 1H NMR monitoring and quantum-chemical calculations. In contrast to the mechanism proposed earlier for nucleophilic vinylic substitution of captodative carbonyl-bearing haloalkenes, this reaction proceeds via either E–Ad or Ad–E sequence depending on the nature of aromatic substituents of the parent styrenes. |
| Keywords: | Reaction mechanisms β-Halo-β-trifluoromethylstyrenes Amines Domino reactions |
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