3,3,3-Trichloropropyl-1-triphenylphosphorane: A Reagent for the Synthesis of (Z)-1,3-Enynes, (Z,Z)-1-Chloro-1,3-dienes, and 1,3-Diynes
Maheswaran S. Karatholuvhu and Philip L. Fuchs*
*Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette,
Indiana 47907, Email: pfuchs
purdue.edu
M. S. Karatholuvhu, P. L. Fuchs, J. Am. Chem. Soc., 2004, 126, 14314-14315.
DOI: 10.1021/ja045112v
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Abstract
Deprotonation of 3,3,3-trichloropropyl-1-triphenylphosphonium chloride generates the corresponding phosphorane, 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.
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Key Words
Z-Alkenes, 1,3-Dienes, 1,3-Enynes, Haloalkynes
ID: J48-Y2004-1810
