Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5226765 | Tetrahedron | 2009 | 6 Pages |
Abstract
2-Aryl-1-vinylpyrroles in acetone, THF and benzene react with tetracyanoethene chemo- and regiospecifically across the vinyl group to give 3-(2-arylpyrrol-1-yl)-1,1,2,2-cyclobutanetetracarbonitriles in 88-94% yield. The latter, upon recrystallization from EtOH, eliminates HCN and entirely rearranges to afford stereospecifically trans-(3E)-4-(2-arylpyrrol-1-yl)-1,3-butadiene-1,1,2-tricarbonitriles. In DMSO, along with the above [2+2]-cycloaddition, tricyanovinylation of the pyrrole ring occurs to form the corresponding 3- and 5-tricyanovinylpyrroles, the product ratio being dependent on the substituents in the pyrrole ring and the reaction conditions.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Boris A. Trofimov, Lyubov' N. Sobenina, Vladislav N. Drichkov, Igor' A. Ushakov, Al'bina I. Mikhaleva,