Hyperconjugative pi-aromaticity: How to make cyclopentadiene aromatic

Authors
Nyulaszi, L Schleyer, PV
Citation
L. Nyulaszi et Pv. Schleyer, Hyperconjugative pi-aromaticity: How to make cyclopentadiene aromatic, J AM CHEM S, 121(29), 1999, pp. 6872-6875
Citations number
41
Categorie Soggetti
Chemistry & Analysis",Chemistry
Journal title
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
ISSN journal
00027863 → ACNP
Volume
121
Issue
29
Year of publication
1999
Pages
6872 - 6875
Database
ISI
SICI code
0002-7863(19990728)121:29<6872:HPHTMC>2.0.ZU;2-F
Abstract
Cyclopentadienes, when 5,5-disubstituted with electropositive groups, have considerably enhanced cyclic conjugation in comparison with the parent mole cule, C5H6. According to various aromaticity indices, 5,5-distannylcyclopen tadiene is nearly as aromatic as furan. Previous observations on the reacti vity were interpreted in the light of the observed aromatic stabilization.