July 1, 1999Journal of the American Chemical Society191 citations
View Full PaperHyperconjugative π-Aromaticity: How To Make Cyclopentadiene Aromatic
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Abstract
Cyclopentadienes, when 5,5-disubstituted with electropositive groups, have considerably enhanced cyclic conjugation in comparison with the parent molecule, C 5 H 6 . According to various aromaticity indices, 5,5-distannylcyclopentadiene is nearly as aromatic as furan. Previous observations on the reactivity were interpreted in the light of the observed aromatic stabilization.