arylsulfone

Arylsulfones are sulfone compounds in which one or both substituents attached to the sulfonyl group are aryl rings. The most common members are diaryl sulfones, with the general formula Ar-SO2-Ar'. In diaryl sulfones, two aryl groups are bound to the sulfur atom (sulfur in the +6 oxidation state)via the sulfonyl (SO2) linkage. The term can also cover aryl-substituted sulfones where one side is an aryl group and the other a different substituent.

Structure and properties: The sulfonyl group confers high polarity and chemical stability to arylsulfones. The S=O bonds make the molecules relatively resistant to oxidation and reduction under normal conditions. Diaryl sulfones typically have high melting and boiling points and serve as stable, inert backbones in organic synthesis and materials.

Synthesis: A common preparation route is the oxidation of sulfides (thioethers) to sulfones using oxidants such as Oxone, hydrogen peroxide, or peracids. For example, diphenyl sulfide can be oxidized to diphenyl sulfone. Other approaches include coupling strategies that form the sulfonyl linkage between aryl partners, though oxidation of sulfides remains a standard method for diaryl sulfones.

Applications: Diphenyl sulfone is a widely cited example and is used as a high-temperature solvent and heat-transfer fluid, as well as a versatile building block in polymer and pharmaceutical synthesis. Diaryl sulfones also appear as intermediates in the preparation of various specialty chemicals, dyes, and pharmaceutical agents. A well-known example is dapsone (4,4'-diaminodiphenyl sulfone), an antimicrobial agent.

Safety and scope: As with many aromatic sulfones, arylsulfones are typically handled as stable, relatively inert chemicals, though individual compounds can vary in toxicity and handling requirements.