An unusual reaction of a pyridinium ylide with 1,1-dicyanoethylene derivatives

A reaction of pyridinium perfluorophenacylide generated from pyridinium salt 1 with 1,1-dicyanoethylene derivatives 2 produced unusual products 3, which have an ylide structure with a cyano group at the C2 and a cis-acrylonitrile moiety at the o-position of the perfluorophenyl group. A plausible mec...

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Bibliographic Details
Published inChemistry letters Vol. 37; no. 6; pp. 628 - 629
Main Authors Yamada, Shinji, Ohta, Emiko
Format Journal Article
LanguageEnglish
Published TOKYO Chemical Soc Japan 05.06.2008
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
INDOLIZINES
METHYLIDE
AB-INITIO
X-RAY
DIFFRACTION
STEREOSELECTIVE-SYNTHESIS
CYCLOPROPANES
N-YLIDES
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Summary:A reaction of pyridinium perfluorophenacylide generated from pyridinium salt 1 with 1,1-dicyanoethylene derivatives 2 produced unusual products 3, which have an ylide structure with a cyano group at the C2 and a cis-acrylonitrile moiety at the o-position of the perfluorophenyl group. A plausible mechanism involving intramolecular aromatic nucleophilic substitution and 1,3-migration of the cyano group is proposed for this reaction.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.2008.628