The Dieckmann Condensation (Including the Thorpe-Ziegler Condensation)
Published Online: 15 MAR 2011
Copyright © 2004 by Organic Reactions, Inc. Published by John Wiley & Sons, Inc.
How to Cite
Schaefer, J. P. and Bloomfield, J. J. 2011. The Dieckmann Condensation (Including the Thorpe-Ziegler Condensation). Organic Reactions. 15:1:1–203.
- Published Online: 15 MAR 2011
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The Dieckman condensation is an acetoacetic ester condensation in which a dicarboxylic ester is cyclized to a beta-ketonic ester through the action of a base. The dicarboxylic ester must have at least one alpha-hydrogen atom and the carbalkoxy groups must be situated that cyclization will result in a 4-membered ring or larger ring. Discovery and development of the reaction are generally credited to Dieckmann, who found that heating an adipic or a pimelic ester with sodium and a trace alcohol led to cyclization with formation of a cyclopentanone or a cyclohexanone. The Dieckmann condensation has proved useful for the preparation of a variety of carbocyclic and heterocyclic ketones and has been extended to the synthesis of 7 and 8-membered rings.
- Dieckman condensation;
- Michael condensation;
- intermolecular ester;
- acyloin condensation;