| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5279369 | Tetrahedron Letters | 2006 | 4 Pages |
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.
Download full-size image
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Boris A. Trofimov, Ol'ga V. Petrova, Lyubov' N. Sobenina, Igor' A. Ushakov, Al'bina I. Mikhaleva, Yurii Yu. Rusakov, Leonid B. Krivdin,