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The Synthesis of Acetylenes

  1. Thomas L. Jacobs

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or005.01

Organic Reactions

Organic Reactions

How to Cite

Jacobs, T. L. 2011. The Synthesis of Acetylenes. Organic Reactions. 5:1:1–78.

Author Information

  1. University of California, Los Angeles

Publication History

  1. Published Online: 15 MAR 2011

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Abstract

Many advances have been made in recent years in the methods for the synthesis of acetylenes and many compounds are now rather readily available in the pure state. Acetylene was first prepared by Davy, who treated acetylide with water. Propyne, the first substituted acetylene was obtained in 1861. At the present time alkynes are usually synthesized by the alkylation of sodium acetylide or substituted metallic acetylides, often in liquid ammonia and 1-Alkynes are also obtained by dehydrohalogenation of suitable halides with sodium amide or in certain cases by ethanolic alkali. The present discussion will be limited to methods for the creation of a carbon-carbon triple bond and to the alkylation of metallic acetylides.

Keywords:

  • acetylenes;
  • dehydrohalogenation;
  • potassium hydroxide;
  • sodium amide;
  • ammonia;
  • triple bond;
  • metallic derivatives;
  • 1-Alkyenes;
  • side reactions;
  • tolans;
  • disubstituted acetylenes;
  • monosubstituted acetylene;
  • experimental procedures