S-phenyl thiobenzoates

S-phenyl thiobenzoate typical procedure in the presence of diphenyl disulphide. Photolysis of the telluroester (Ar = 4-FCgH4) in the presence of 6 equiv of diphenyl disulphide according to the standard for the formation of selenoesters gave 71% of the thiobenzoate after chromatography on silica gel (eluent hexane/ ethyl acetate, 9 1). The product had a melting point and spectral characteristics in accordance with those described in the literature. 

Hydroxyalkylphenones Phenylglyoxylates S-Phenyl thiobenzoates O-Acyl-a-oximo ketones... 

A mixture of 2-(phenoxymethyl)oxirane, S-phenyl thiobenzoate, and a little Bu4NBr in dry DMF stirred at 110° for 25 h - 2-benzoyloxy-3-(phenylthio)propyl phenyl ether. Y 71% (82.4% conversion). F.e. and with 18-crown-6-metal complexes s. T. lizawa et al., Bull. Chem. Soc. Japan 62, 597-8 (1989) with a polymer-based phosphonium salt cf. Chem. Letters 1988, 1605-8. 

Arylthiolic acid esters. A soln. of iodobenzene and triethyltin phenylmercaptide in hexamethylphosphoramide stirred in the presence of a little PhPdI(PPii3)2 at 20° under 1 atm. CO for 24 h - S-phenyl thiobenzoate. Y 78%. Nitro-subst. ar. iodides gave the corresponding ar. thioethers. F.e.s. Y.V. Gulevich et al., Zh. Org. Khim. 24, 2126-32 (1988). 

These include thiobenzoates, thiocarbonylimidazolides, and phenyl thionocarbonate esters.6 The S-methyl xanthate ester is a particularly convenient intermediate to prepare because of its ease of formation and the low cost of the reagents. Its use is precluded, however, by the presence of base-labile protecting groups and, in such cases, the thiocarbonylimidazolide or phenyl thionocarbonate ester will generally prove satisfactory. Additional methods for the radical deoxygenation of alcohols are described in a review by Hartwig.7... 

A water-cooled mixture of allylbenzene and O-methyl thiobenzoate irradiated 10 days with a 400 w. high-pressure Hg-lamp under CO in a sealed Pyrex vessel, evaporated under reduced pressure, and the residue diromatographed on silica-gel with -hexane as eluent phenethyl phenyl ketone. Y ca. 100%. - An allylic methylene group is necessary for the reaction. F. e. s. A. Ohno, T. Koizumi, and Y. Akazaki, Tetrah. Let. 7972, 4993. 

---