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Reppe Cyclization

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr531

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Reppe Cyclization. Comprehensive Organic Name Reactions and Reagents. 531:2358–2361.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The nickel complex-catalyzed [2+2+2+2] cyclotetramerization of acetylene to cyclooctatetraene (COT) is generally known as the Reppe cyclization. This reaction demonstrates the efficiency for organometallic complex-catalyzed reactions. It has been reported that nickel catalyst does not work for disubstituted alkynes. Generally, this reaction does not hold regioselectivity and often, this reaction is accompanied with side reactions yielding benzene derivatives. This reaction has been modified by use of the sterically hindered 1,2-diaza diene nickel complex, Ni(dad)2 as catalyst to improve the regioselectivity. This reaction has general application in the preparation of cyclooctatetraene derivatives.

Keywords:

  • cyclooctatetraene (COT);
  • 1,2-diaza diene nickel complex;
  • 1-methyl-2-phenyl-acetylene;
  • turnover number