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]
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.
^Truce, W. E.; Vriesen; C. W. (1953). "Friedel—Crafts Reactions of Methanesulfonyl Chloride with Benzene and Certain Substituted Benzenes". J. Am. Chem. Soc.75 (20): 5032–5036.
doi:
10.1021/ja01116a043.
^Répichet, S.; Le Roux, C.; Hernandez, P.; Dubac, J.; Desmurs, J. R. (1999). "Bismuth(III) Trifluoromethanesulfonate: An Efficient Catalyst for the Sulfonylation of Arenes". The Journal of Organic Chemistry. 64 (17): 6479–6482.
doi:
10.1021/jo9902603.
^Truce, W. E.; Milionis, J. P. (1952). "Friedel-Crafts Cyclization of ω-Phenylalkanesulfonyl Chlorides". J. Am. Chem. Soc.74 (4): 974–977.
doi:
10.1021/ja01124a031.
^C. W. Ferry, J. S. Buck, R. Baltzly (1942). "4,4'-Diaminodiphenylsulfone". Org. Synth. 22: 31.
doi:
10.15227/orgsyn.022.0031.{{
cite journal}}: CS1 maint: multiple names: authors list (
link)
^Carey, Francis A.; Sundberg, Richard J. (2007). Advanced Organic Chemistry. Berlin: Springer.
ISBN978-0-387-68354-6.
^Craig, Charles R.; Stitzel, Robert E. (2004). Modern Pharmacology with Clinical Applications. Hagerstwon: Lippincott Williams & Wilkins.
ISBN978-0-7817-3762-3.
^Drill, Victor Alexander; Di Palma, Joseph R. (1971). Drill's Pharmacology in Medicine. New York: McGraw-Hill.
ISBN978-0-07-017006-3.