The Acyloin Condensation
Published Online: 15 MAR 2011
Copyright © 2004 by Organic Reactions, Inc. Published by John Wiley & Sons, Inc.
How to Cite
Bloomfield, J. J., Owsley, D. C. and Nelke, J. M. 2011. The Acyloin Condensation. Organic Reactions. 23:2:259–404.
- Published Online: 15 MAR 2011
The acyloin condensation usually involves the reductive dimerization of a carboxylic ester, although acid chlorides and the anhydrides have been used. The reducing agent is in an alkali metal and the product is an ene-diolate. Two gram-atoms of metal are required for each mole of ester with the concomitant formation of a mole of akoxide and one-half mole of the ene-diolate. Oxidation of acyloins to diketoes can be accomplished by a variety of reagents. Acyloins can be reduced to ketones by various modifications of the Clemmenson technique. Under mild conditions the ketone will dominate. This chapter presents a complete picture of both the linear and cyclic acyloin condensation with particular emphasis on developments since 1960. The discussion is closely limited to the acyloin condensation and its modifications.
- dicarboxylic acids;
- monocarboxyl acids;
- heterocyclic esters;
- experimental procedures