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In organic chemistry, a sulfone is a organosulfur compound containing a sulfonyl () functional group attached to two carbon atoms. The central hexavalent sulfur atom is to each of two oxygen atoms and has a single bond to each of two carbon atoms, usually in two separate hydrocarbon .
Sulfones are prepared under conditions used for Friedel–Crafts reactions using sources of derived from sulfonyl halides and sulfonic acid anhydrides. Lewis acid catalysts such as and are required.
Sulfones have been prepared through nucleophilic displacement of by :
Sulfones are strongly electron-withdrawing, and
are electrophilic . (2025). 9780471936237 ISBN 9780471936237
The behavior of the locant depends on context. Non-nucleophilic bases deprotonate to an enolate-like carbanion. Contrariwise, on the sulfone oxygens give a Pummerer-like electrophile that undergoes nucleophilic substitution.
Sulfones can also undergo reductive desulfonylation.
Applications
Sulfolane is used to extract valuable aromatic compounds from petroleum.
Polymers
Some polymers containing sulfone groups are useful engineering plastics. They exhibit high strength and resistance to oxidation, corrosion, high temperatures, and creep under stress. For example, some are valuable as replacements for copper in domestic hot water plumbing. Precursors to such polymers are the sulfones bisphenol S and 4,4′-dichlorodiphenyl sulfone.
Pharmacology
Examples of sulfones in pharmacology include dapsone, a drug formerly used as an antibiotic to treat leprosy, dermatitis herpetiformis, tuberculosis, or pneumocystis pneumonia (PCP). Several of its derivatives, such as promin, have similarly been studied or actually been applied in medicine, but in general sulfones are of far less prominence in pharmacology than for example the sulfonamides. (2025). 9780781737623, Lippincott Williams & Wilkins. ISBN 9780781737623 (1971). 9780070170063, McGraw-Hill. ISBN 9780070170063
See also
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