Triphenylphosphine Sulfide


[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

Purification: recrystallization from ethanol2,4 or aqueous acetone.3,5

Conversion of Epoxides into Thiiranes.1

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

Conversion of Phenols into Dihydric Phenols.6

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).

1. Chan, T. H.; Finkenbine, J. R. JACS 1972, 94, 2880.
2. Screttas, C.; Isbell, A. F. JOC 1962, 27, 2573.
3. Olah, G. A.; Berrier, A.; Ohannesian, L. NJC 1986, 10, 253.
4. Michaelis, A.; Gleichmann, L. CB 1882, 15, 801.
5. Olah, G. A.; Hehemann, D. JOC 1977, 42, 2190.
6. Takahashi, K.; Uohama, M.; Akiyama, T. Eur. Patent Appl. 468 477 (CA 1992, 116, 193 896s).

Darrin L. Mayhew & Derrick L. J. Clive

University of Alberta, Edmonton, Canada

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