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The Willgerodt Reaction

  1. Marvin Carmack1,
  2. M. A. Spielman2

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or003.02

Organic Reactions

Organic Reactions

How to Cite

Carmack, M. and Spielman, M. A. 2011. The Willgerodt Reaction. Organic Reactions. 3:2:83–107.

Author Information

  1. 1

    University of Pennsylvania

  2. 2

    Abbott Laboratories

Publication History

  1. Published Online: 15 MAR 2011

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Abstract

The name of Conrad Willgerodt is associated with a group of closely related reactions which have a common feature the conversion of a carbonyl compound into an amide with the same number of carbon atoms. The original process involved the reaction of an appropriately substituted alkyl aryl ketone with an aqueous solution of yellow ammonium polysulfide at an elevated temperature to form an aryl-substituted aliphatic acid amide, together with a smaller amount of the corresponding ammonium salt of the carboxylic acid. The Kindler variation promises to be more useful. It consists of heating a ketone with approximately equimolecular amounts of sulfur and dry amine.

Keywords:

  • Willgerodt reaction;
  • ammonium polysulfide;
  • organic solvents;
  • Kindler modification;
  • by-products;
  • amines;
  • sulfur;
  • experimental procedures