The intramolecular condensation of a diester, producing a cyclic β-keto ester, is called the Dieckmann condensation. The base abstracts an α-proton from one of the esters, yielding an enolate ion that attacks the other ester, forming a tetrahedral intermediate. Alkoxide ion is released, followed by the formation of a second base-mediated enolate ion. An acid work-up affords the final cyclic β-keto ester.

  • Reagents: Metal Alkoxide, Alkoxide Base, Acid Work-up
  • Reactant: Diester with α-Hydrogens
  • Product: Cyclic β-Keto Ester
  • Type of Reaction: Condensation


Top Citations

Original Paper

Related Reactions

  • Clasien Condensation

Related Compounds

  • Metal Alkoxide
  • Alkoxide Base
  • Acid Work-up
By shuhan yang


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