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Dieckmann Condensation

Definition: What is Dieckmann Condensation?

The Dieckmann condensation is an organic reaction which is used to form a carbon-carbon bond between two tethered ester groups using an alkoxide base in alcohol. The resulting product is a cyclic β-ketoester. This reaction is an intermolecular form of Claisen condensation [1-3].

Dieckmann Condensation

The history of Dieckmann condensation goes back to 1894 when German chemist Walter Dieckmann first reported it in a journal.

Examples of Dieckmann Condensation

Examples of Dieckmann condensation include conversion of diethyl adipate into ethyl 2-oxocyclopentanecarboxylate and diethyl heptanedioate (pimelate) into 2-propanoylcyclohexanone [4-5].

Dieckmann Condensation Examples

Mechanism of Dieckmann Condensation

The mechanism is similar to that of Claisen condensation. A strong base removes the alpha proton resulting in an enolate. The enolate then attacks the carbonyl carbon of another ester molecule, resulting in a cyclic β-ketoester and regenerating the conjugate base. The base then deprotonates the cyclic compounds, and an acid workup is required to produce the final cyclic β-ketoester [6-8].

Dieckmann Condensation Mechanism

Applications of Dieckmann Condensation

Dieckmann condensation is used in the preparation of cyclic indole. There has been a report of preparing five-membered pyrroles through this condensation method [9].

References

  1. Definition – Name-reaction.com
  2. Definition – Organic-chemistry.org
  3. Definition – Chem.ucalgary.ca
  4. Example – Chem.libretexts.org
  5. Example – Chtf.stuba.sk
  6. Mechanism – Ochempal.org
  7. Mechanism – Chem.ucla.edu
  8. Mechanism – Synarchive.com
  9. Application – Conservancy.umn.edu

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