Dieckmann condensation

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The Dieckmann condensation
The Dieckmann condensation

The Dieckmann condensation is the intramolecular chemical reaction of diesters with base to give β-ketoesters.[1][2][3][4][5]. It is named after the German chemist Walter Dieckmann (1869–1925). The equivalent intermolecular reaction is the Claisen condensation.

Dieckmann Condensation reaction mechanism for the example given.
Dieckmann Condensation reaction mechanism for the example given.

[edit] Reaction Mechanism

The acidic hydrogen between the two carbonyl groups is deprotonated in step four. Protonation with a Brønsted-Lowry acid (H3O+ for example) re-forms the β-keto ester. [6] This deprotonation step is the driving force for this reaction.

[edit] See also

[edit] References

  1. ^ Dieckmann, W. Ber. 1894, 27, 102 & 965
  2. ^ Dieckmann, W. Ber. 1900, 33, 595 & 2670
  3. ^ Dieckmann, W. Ann. 1901, 317, 51 & 93
  4. ^ Schaefer, J. P.; Bloomfield, J. J. Org. React. 1967, 15, 1-203. (Review)
  5. ^ Davis, B. R.; Garrett, P. J. Comp. Org. Syn. 1991, 2, 806-829. (Review)
  6. ^ Janice Gorzynski Smith. Organic Chemistry: Second Ed. 2008. pp 932-933.