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Leuckart Thiophenol Synthesis

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr391

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Leuckart Thiophenol Synthesis. Comprehensive Organic Name Reactions and Reagents. 391:1743–1746.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The synthesis of thiophenol involves the reaction between a diazonium salt and potassium ethylxanthate to form diazonium ethylxanthate, which decomposes upon heating to both diarylthiocarbonate and aryl xanthate that then afford thiophenol upon alkaline hydrolysis. This reaction is known as the Leuckart thiophenol synthesis. Several conditions of the reaction have been discussed, which influences the yield of the reaction. It has been found that the best yield of diarylthiocarbonate can be obtained when a 1:1 ratio of diazonium salt and potassium ethyl xanthate are used, and the increase of acidity lowers the yield of diarylthiocarbonate. This reaction is useful for the preparation of thiophenols.

Keywords:

  • diazonium salt;
  • aryl carbonium;
  • aryl xanthates;
  • ethanol