Title of article
Easy α- to β-migration of an enol moiety on a pyrrole ring
Author/Authors
Trofimov، نويسنده , , Boris A. and Petrova، نويسنده , , Ol’ga V. and Sobenina، نويسنده , , Lyubov’ N. and Ushakov، نويسنده , , Igor’ A. and Mikhaleva، نويسنده , , Al’bina I. and Rusakov، نويسنده , , Yurii Yu. and Krivdin، نويسنده , , Leonid B.، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2006
Pages
4
From page
3645
To page
3648
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.
Keywords
Enols , ?- to ?-Migration , 2-Vinylpyrroles , Ethylthio group , hydroxide
Journal title
Tetrahedron Letters
Serial Year
2006
Journal title
Tetrahedron Letters
Record number
1850404
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