Easy α- to β-migration of an enol moiety on a pyrrole ring |
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| Authors: | Boris A. Trofimov,Ol&rsquo ga V. Petrova,Lyubov&rsquo N. Sobenina,Igor&rsquo A. Ushakov,Al&rsquo bina I. Mikhaleva,Yurii Yu. Rusakov,Leonid B. Krivdin |
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| Affiliation: | A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Street, Irkutsk 664033, Russian Federation |
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| Abstract: | Functionalized pyrrolic enols, 2-(2,2-dicyano-1-hydroxyethenyl)-1-methylpyrroles, synthesized from 2-ethenylpyrroles by a nucleophilic SEt-OH exchange, upon heating (75-142 °C) are readily rearranged to their 3-isomers in near to quantitative yield. The inter or intramolecular auto-protonation of a pyrrole ring by the acidic enol hydroxyl to form a mesomeric pyrrolium cation or zwitterion is suggested to be a key step in the rearrangement. |
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| Keywords: | 2-Vinylpyrroles Ethylthio group Hydroxide Enols α- to β-Migration |
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