Standard Article

Wichterle Reaction

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr669

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Wichterle Reaction. Comprehensive Organic Name Reactions and Reagents. 669:3003–3007.

Publication History

  1. Published Online: 15 SEP 2010

Chemistry Terms

Choose one or more boxes to highlight terms.

Abstract

This reaction is a modification of the Robinson annulation in which 1,3-dichloro-cis-2-butene is applied as the equivalent of methyl vinyl ketone to avoid the potentially undesirable condensation and polymerization during the step of the Michael addition, and is generally referred to as the Wichterle reaction. The most important modification for this reaction is the application of 2-trimethylsilyl-4-iodo-2-cis-butene for the annulation. This reaction has been applied for preparation of fused cyclic compounds.

Keywords:

  • γ-chlorocrotyl derivatives;
  • 1,3-dichloro-cis-2-butene;
  • methyl vinyl ketone;
  • sulfuric acid