ON THE INFLUENCE OF SPIROCONJUGATION AND ELECTRON-WITHDRAWING EFFECTSON THE FRONTIER ORBITAL ENERGIES OF 5-SUBSTITUTED CYCLOPENTADIENES

Authors
RAMAN JV NIELSEN KE RANDALL LH BURKE LA DMITRIENKO GI
Citation
Jv. Raman et al., ON THE INFLUENCE OF SPIROCONJUGATION AND ELECTRON-WITHDRAWING EFFECTSON THE FRONTIER ORBITAL ENERGIES OF 5-SUBSTITUTED CYCLOPENTADIENES, Tetrahedron letters, 35(33), 1994, pp. 5973-5976
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
33
Year of publication
1994
Pages
5973 - 5976
Database
ISI
SICI code
0040-4039(1994)35:33<5973:OTIOSA>2.0.ZU;2-H
Abstract
Ab initio calculations reveal that the influence of spiroconjugation o n the HOMO of 5-substituted cyclopentadienes is weak relative to elect ron withdrawing effects and that both the HOMO and LUMO energy levels can be lower than in cyclopentadiene contrary to the predictions of qu alitative perturbation theory. In accord with these theoretical result s, the reaction of 5,5-dicyanocyclopentadiene with cyclopentadiene yie lds only heterodimers.