Collect. Czech. Chem. Commun. 1993, 58, 2229-2244

The Wichterle Reaction

Miloš Hudlický

Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, Virginia 24061, U.S.A.


The Wichterle reaction is a conversion of vinylic chlorides to ketones by sulfuric acid. Most of the applications are transformations of γ-chlorocrotyl (3-chloro-2-butenyl) derivatives to 3-oxobutyl derivatives. The ketones thus formed may undergo subsequent reactions in compounds containing reactive centers. Thus intramolecular aldol-type condensations occur in compounds containing carbonyl groups, and Friedel-Crafts-type cyclizations in compounds containing aromatic rings. The reaction can be used as an alternative to Robinson's annelation.