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The Dieckmann Condensation (Including the Thorpe-Ziegler Condensation)

  1. John P. Schaefer1,
  2. Jordan J. Bloomfield2

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or015.01

Organic Reactions

Organic Reactions

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.

Author Information

  1. 1

    The University of Arizona

  2. 2

    The University of Oklahoma

Publication History

  1. Published Online: 15 MAR 2011

Chemistry Terms

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Abstract

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.

Keywords:

  • Dieckman condensation;
  • cyclizations;
  • Michael condensation;
  • intermolecular ester;
  • alkylation;
  • acyloin condensation;
  • failures