Tracer Study of the Reactions of Diphenyl Sulfone and Diphenyl Sulfoxide with Diphenyl Disulfide

Abstract

Diphenyl sulfoxide and diphenyl sulfone were found to react with diphenyl disulfide at elevated temperatures, forming in both reactions diphenyl sulfide and sulfur dioxide. On the basis of 35S and 14C tracer experiments, these reactions were found to proceed through quite different mechanistic routes, viz., S–O bond fission in the case of sulfoxide and C–S bond fission in sulfone. The reactions apparently proceed through the attack of the thiyl radical on the sulfoxide and sulfone functions. Further mechanistic details of the reactions are discussed.

Cyclic Aromatic Disulfide Oligomers: Synthesis and Characterization

“…14n has the least thermal stability, which is due to loss of sulfur dioxide. Oae et al have shown that the reaction of diphenyl sulfone and diphenyl disulfide produces sulfur dioxide at 300 °C . It can be seen that the initial weight loss of cyclic oligomer 14n is roughly equal to the weight loss of sulfur dioxide.…”

Rhenium-Catalyzed Oxidation of Thiols and Disulfides with Sulfoxides

“…Changing the sulfoxide component of the catalytic system from Me 2 SO to Ph 2 SO resulted in rapid oxidation of disulfides to the products indicated in Table . Thiosulfonate products were isolated from the catalytic Re(Ph 2 SO) oxidation of acyclic alkyl and aryl disulfides …”

N-Bromosuccinimideand Iodine Catalyzed Highly Efficient Deoxygenation ofSulfoxides to Thioethers Using 3-Mercaptopropionic Acid under Mild ReactionConditions

“…3j,k Among the reported protocols, sulfur compounds such as thiols, 4 sulfides, 5 disulfides, 6 thionyl chloride, 7 elemental sulfur, 8 and 1,3dithianes 9 have been used for the conversion of sulfoxides to thioethers. However, many of these methods suffer from drawbacks such as long reaction time, [4][5][6] harsh acidic conditions, 4,7 high temperature, 8 or difficult work-up procedures. 4,9 Therefore, there is still a demand for the development of a new efficient method for this transformation using inexpensive and common laboratory reagents.…”