1,4-diazabicyclo[2.2.2]octane-catalyzed self- and cross- condensation of α-acetylenic ketones

P. Veeraraghavan Ramachandran, Michael T. Rudd, M. Venkat Ram Reddy

Research output: Contribution to journalArticlepeer-review

21 Scopus citations


3-Butyn-2-one condenses with itself in the presence of 0.1 molar equiv of Dabco providing 80% yield of E-3-(1-buten-3-yn-2-oxy)-buten-2-one. Substitution at the acetylene terminus prevents the condensation. However, such ketones can be condensed with terminal acetylenic ketones to provide the cross-coupled products in high yields.

Original languageEnglish (US)
Pages (from-to)3819-3822
Number of pages4
JournalTetrahedron Letters
Issue number20
StatePublished - May 14 1999

Bibliographical note

Funding Information:
The financial assistance from the Purdue Borane Research Fund is gratefully


  • Condensation
  • Dabco
  • Divinyl ether
  • Trialkylamine
  • α-acetylenic ketones


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