Vinylic nucleophilic substitution in functionalized 2-vinylpyrroles: a route to a new family of stable enols |
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| Authors: | Boris A Trofimov Olga V Petrova Vladislav N Drichkov Igor' A Ushakov Olga N Kazheva Anatolii N Chekhlov Oleg A Dyachenko |
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| Institution: | a A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, Russian Federation
b Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 N.N. Semenov Ave, Chernogolovka 142432, Russian Federation |
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| Abstract: | 2-(2-Cyano-1-ethylthioethenyl)pyrroles easy exchange their ethylthio group for hydroxyl (NaOH, H2O-methanol, 40-45 °C, 1 h) to give 2-(2-cyano-1-hydroxyethenyl)pyrroles, a new family of stable enols, in 50-94% yields. The vinylic nucleophilic substitution proceeds at the double bond of both the starting pyrroles and their cyclic isomers, 3-iminopyrrolizines. X-ray structure analysis and NMR spectra show the enols to be stabilized by exceptionally strong intramolecular H-bonding. |
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| Keywords: | 2-Vinylpyrroles 3-Iminopyrrolizines Vinylic nucleophilic substitution |
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