Organic Chemistry Portal



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:

M. S. Karatholuvhu, P. L. Fuchs, J. Am. Chem. Soc., 2004, 126, 14314-14315.

DOI: 10.1021/ja045112v

see article for more reactions


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.

see article for more examples

Key Words

Z-Alkenes, 1,3-Dienes, 1,3-Enynes, Haloalkynes

ID: J48-Y2004-1810