Sulfone

A sulfone is a chemical compound containing a sulfonyl functional group attached to two carbon atoms. The central hexavalent sulfur atom is double bonded to each of two oxygen atoms and has a single bond to each of two carbon atoms, usually in two separate hydrocarbon substituents.[1]

Contents

IUPAC name and chemistry

The use of the long-standing alternative spelling sulphone is discouraged by IUPAC; it is definitely undesirable to have two spellings in simultaneous common use, and it was agreed to discontinue the ph spelling as the more archaic.

The general structural formula is R-S(=O)(=O)-R' where R and R' are the organic groups. Sulfides are often the starting materials for sulfones by organic oxidation through the intermediate formation of sulfoxides. For example dimethyl sulfide is oxidized to dimethyl sulfoxide and then to dimethyl sulfone.[1]

In the Ramberg-Bäcklund Reaction and the Julia olefination sulfones are converted to alkenes through the elimination of sulfur dioxide.[2]

Polymers

In recent decades sulfone polymers have gained prominence in the field of engineering plastics. Various polymers are of importance because of properties such as their high strength and their resistance to oxidation, corrosion, high temperatures, and creep under stress. For example, some are valuable as replacements for copper in domestic hot water plumbing.[3]

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 say, the sulfonamides.[4][5]

In the literature, particularly lay literature, sulfones commonly are confused with sulfonamides, though the latter have one carbon and one nitrogen atom attached to the sulfur atom, instead of two carbon atoms. The pharmacological mechanisms accordingly differ from that of the sulfonamides. However, in practice one commonly sees frequent references to dapsone and promin as sulfonamides. Probably this is partly because few pharmaceuticals are in fact sulfones.

See also

References

  1. ^ a b Hornback, Joseph (2006). Organic Chemistry. Australia: Thomson Brooks/Cole. ISBN 9780534389512. 
  2. ^ Francis A. Carey, Richard J. Sundberg (2007). Advanced Organic Chemistry. Berlin: Springer. ISBN 9780387683546. 
  3. ^ Fink, Johannes (2008). High Performance Polymers. Norwich: William Andrew. ISBN 9780815515807. 
  4. ^ Charles R. Craig, Robert E. Stitzel (2004). Modern Pharmacology with Clinical Applications. Hagerstwon: Lippincott Williams & Wilkins. ISBN 9780781737623. 
  5. ^ Victor Alexander Drill, Joseph R.Di Palma (1971). Drill's Pharmacology in Medicine. New York: McGraw-Hill. ISBN 9780070170063.