3,3,3-Trichloropropyl-1-triphenylphosphorane: A Reagent for the Synthesis of (<i>Z</i>)-1,3-Enynes, (<i>Z</i>,<i>Z</i>)-1-Chloro-1,3-dienes, and 1,3-Diynes

Abstract

3,3,3-Trichloropropyl-1-triphenylphosphonium chloride is conveniently prepared from 2-chloroethanol, triphenylphosphine, and trichloroacetic acid. Deprotonation of this reagent generates 3,3,3-trichloropropyl-1-triphenylphosphorane, which reacts with aldehydes to give trichloromethylated (Z)-olefins, which are useful for the synthesis of (Z)-1,3-enynes, (Z,Z)-1-chloro-1,3-dienes, and 1,3-diynes in high yields and stereospecificities.