UNUSUAL FORMATION OF TRICYCLIC ANNULENEDIONES - DIATROPIC CATIONIC 10-PI-ELECTRON SPECIES IN D2SO4

Authors
HIGUCHI H SAKON C ASANO K OJIMA J IYODA M INOUE K YAMAMOTO G
Citation
H. Higuchi et al., UNUSUAL FORMATION OF TRICYCLIC ANNULENEDIONES - DIATROPIC CATIONIC 10-PI-ELECTRON SPECIES IN D2SO4, Journal of the Chemical Society. Perkin transactions. I, (20), 1994, pp. 2915-2920
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
20
Year of publication
1994
Pages
2915 - 2920
Database
ISI
SICI code
0300-922X(1994):20<2915:UFOTA->2.0.ZU;2-F
Abstract
Intramolecular oxidative coupling of ent-1-en-4-ynyl)-6-(1-oxoprop-2-y nyl)cyclohepta-1, 3,5-triene 2 under the Glaser conditions unexpectedl y afforded two tricyclic annulenediones. The unusual structures were d etermined by X-ray crystallographic analysis of the compounds. These a nnulenediones are atropic in CDCl3, but exhibited diatropicity in CF3C O2D and D2SO4 ascribable to the formation of cationic 10 pi-electron s pecies.