Skip to main content
Article
Synthesis of Azulenone Skeletons by Reaction of 2-Phenyl-2-acylketenes [RCO(Ph)CCO] with Alkynyl Ethers:  Mechanistic Aspects and Further Transformations
The Journal of Organic Chemistry (1998)
  • Ronald Brisbois
  • Dean G Brown
  • Thomas R Hoye
Abstract
A method is described for a mild and efficient synthesis of azulenone skeletons via the addition reactions of 2-phenyl-2-acylketenes with 1-alkynyl ethers. A mechanism is presented to account for both azulenone formation as well as the solvent and substrate dependency of a competitive pyrone formation. The azulenone rings have been subsequently transformed into both substituted azulenes or hydroazulenes by derivatization and/or decarboxylation of an angular carboxyl substituent or by hydrogenation.
Disciplines
Publication Date
February 11, 1998
DOI
10.1021/jo9719315
Citation Information
Ronald Brisbois, Dean G Brown and Thomas R Hoye. "Synthesis of Azulenone Skeletons by Reaction of 2-Phenyl-2-acylketenes [RCO(Ph)CCO] with Alkynyl Ethers:  Mechanistic Aspects and Further Transformations" The Journal of Organic Chemistry Vol. 63 Iss. 5 (1998) p. 1630 - 1636 ISSN: 1520-6904
Available at: http://works.bepress.com/ronald_brisbois/17/