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Dieckmann condensation



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

Reaction Mechanism

 

Additional recommended knowledge

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.

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.


See also

 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Dieckmann_condensation". A list of authors is available in Wikipedia.
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