On the Reaction of Triphenylphosphine-Trichloromethyl Compounds with Styrene Oxide

Abstract

The reactions of triphenylphosphine-trichloromethyl compounds with styrene oxide were investigated. Triphenylphosphine-carbon tetrachloride as a trichloromethyl compound gave styrene dichloride C 2D, a-chlorostyrene [3], [chloro (triphenylphosphoranylidene) methyl] triphenylphosphonium chloride C4 J, triphenylphosphine oxide C 5 and chloroform.
The reaction was accelerated in a polar solvent such as acetonitrile. The use of excess triphenylphosphine to styrene oxide in this reaction produced C_2CD in an almost quantitative yield to the exclusion of OD. However, the addition of phenols to this reaction system produced C 3D in a high yield.
The reactions using other trichloromethyl compounds, except he xachloroethane, resulted in the formation of the products analogous to the case of carbon tetrachloride. The use of trichloromethyl compounds having more electron-withdrawing groups increased the ratio of C_2C to [3]. On the other hand, the reaction using hexachloroethane proceeded at room temperature to give C_2C in a quantitative yield. On the basis of these results, the reaction mechanisum was discussed in detail.