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The Acyloins

  1. S. M. McElvain

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or004.04

Organic Reactions

Organic Reactions

How to Cite

McElvain, S. M. 2011. The Acyloins. Organic Reactions. 4:4:256–268.

Author Information

  1. University of Wisconsin

Publication History

  1. Published Online: 15 MAR 2011

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Abstract

Acyloins arre alpha-hydroxy ketones of the general formula, RCHOHCOR, in which R represents an aliphatic analog of benzoins. The term acyloin is commonly used as a class name for the symmetrical keto alcohols and the name of the individual compound is derived by adding the suffix “oin” to the stem name of the acid to which the acyloin corresponds, e.g., acetoin, butyoin, etc. The commonest method of preparation of those acyloins in which the alkyl groups are identical is the reaction of sodium with esters of aliphatic acids in inert solvents. Salts of enediols are produced in this reaction. Other methods of preparation are discussed.

Keywords:

  • acyloins;
  • aliphatic esters;
  • acid chlorides;
  • hydroxy nitriles;
  • nickel carbonyl;
  • halo ketones;
  • allenes;
  • acetylenes;
  • diketones;
  • glycols;
  • glyoxals;
  • photochemical reactions;
  • biological preparations;
  • experimental procedures