[3878-45-3] · C18H15PS · Triphenylphosphine Sulfide · (MW 294.37)
(conversion of epoxides into thiiranes1)
Physical Data: mp 161 °C.2
Solubility: insol hexane, water, ether; sol acetone, benzene, carbon disulfide, chloroform, ethanol.2-5
Form Supplied in: white solid; commercially available.
Preparative Methods: prepared by a number of methods; most easily prepared from Triphenylphosphine and Sulfur,4 or from benzene, sulfur, and Phosphorus(III) Chloride in the presence of Aluminum Chloride.5
Addition of Trifluoroacetic Acid (1 equiv) to a benzene solution of an epoxide and triphenylphosphine sulfide (1 equiv or an excess) serves to convert the epoxide into the corresponding episulfide (eq 1). The reaction is stereospecific, and can also be done using tributylphosphine sulfide (eq 2).1
Phenols can be converted into mixtures of dihydric phenols using Hydrogen Peroxide, in the presence of a ketone, and a catalytic amount of triphenylphosphine sulfide (eq 3).
Darrin L. Mayhew & Derrick L. J. Clive
University of Alberta, Edmonton, Canada