Hyperconjugative π-Aromaticity:  How To Make Cyclopentadiene Aromatic

Cyclopentadienes, when 5,5-disubstituted with electropositive groups, have considerably enhanced cyclic conjugation in comparison with the parent molecule, C5H6. According to various aromaticity indices, 5,5-distannylcyclopentadiene is nearly as aromatic as furan. Previous observations on the reacti...

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Bibliographic Details
Published in:Journal of the American Chemical Society 1999-07, Vol.121 (29), p.6872-6875
Main Authors: Nyulászi, László, Schleyer, Paul von Ragué
Format: Article
Language:English
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Summary:Cyclopentadienes, when 5,5-disubstituted with electropositive groups, have considerably enhanced cyclic conjugation in comparison with the parent molecule, C5H6. 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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja983113f