Sulfone
In
Synthesis and reactions
By oxidation of thioethers and sulfoxides
Sulfones are typically prepared by
From SO2
Sulfur dioxide is a convenient and widely used source of the sulfonyl functional group. Specifically, Sulfur dioxide participates in cycloaddition reactions with dienes.[3] The industrially useful solvent sulfolane is prepared by addition of sulfur dioxide to buta-1,3-diene followed by hydrogenation of the resulting sulfolene.[4]
From sulfonyl and sulfuryl halides
Sulfones are prepared under conditions used for
Sulfones have been prepared by
Reactions
Sulfone is a relatively inert functional group, typically less oxidizing and 4
Sulfones can also undergo desulfonylation.
Applications
Sulfolane is used to extract valuable aromatic compounds from petroleum.[4]
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.[11] 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.[13][14]
See also
- Organosulfur chemistry
- Sulfonanilide
- Sulfoxide
- Sulfonic acid (–OH substituent)
References
- ^ ISBN 978-0-534-38951-2.
- .
- .
- ^ ISBN 978-3527306732.
- .
- .
- .
- doi:10.15227/orgsyn.022.0031.)
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: CS1 maint: multiple names: authors list (link - ISBN 978-0-387-68354-6.
- ^ Smith (2020), March's Organic Chemistry, rxn. 17-10.
- ISBN 978-0-8155-1580-7.
- ISBN 9780781768795. Archivedfrom the original on 2016-03-04.
- ISBN 978-0-7817-3762-3.
- ISBN 978-0-07-017006-3.