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 ,
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
