Issue 20, 1994

Unusual formation of tricyclic annulenediones: diatropic cationic 10π-electron species in D2SO4

Abstract

Intramolecular oxidative coupling of 1-(3-oxopent-1-en-4-ynyl)-6-(1-oxoprop-2-ynyl)cyclohepta-1,3,5-triene 2 under the Glaser conditions unexpectedly afforded two tricyclic annulenediones. The unusual structures were determined by X-ray crystallographic analysis of the compounds. These annulenediones are atropic in CDCl3, but exhibited diatropicity in CF3CO2D and D2SO4 ascribable to the formation of cationic 10π-electron species.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1994, 2915-2920

Unusual formation of tricyclic annulenediones: diatropic cationic 10π-electron species in D2SO4

H. Higuchi, C. Sakon, K. Asano, J. Ojima, M. Iyoda, K. Inoue and G. Yamamoto, J. Chem. Soc., Perkin Trans. 1, 1994, 2915 DOI: 10.1039/P19940002915

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