S. Miyano, Y. Izumi, Katsuo Fujii
Apr 1, 1979
Citations
0
Influential Citations
22
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
Chloromethyltriphenylphosphonium iodide has been prepared by the reaction of chloroiodomethane with triphenylphosphine. Upon treatment with potassium t-butoxide in t-butyl alcohol, the phosphonium iodide was converted into chloromethylenetriphenylphosphorane; this in turn was used for the Wittig reaction of aldehydes and ketones into the corresponding chloroolefins of the type RCH=CHCl and RR′C=CHCl in good to moderate yields. The configurations of these chloroolefins were assigned on the basis of NMR spectral studies. Direct conversion of benzaldehyde into phenylacetylene was also achieved using the phosphonium salt and excess potassium t-butoxide.