Vinyl sulfone

In organic chemistry, a vinyl sulfone is a functional group consisting of a vinyl group bonded to a sulfone group. Specific compounds containing this functional group are divinyl sulfone,^[1] phenyl vinyl sulfone,^[2] methyl vinyl sulfone,^[3] and ethyl vinyl sulfone.^[4]

The sulfone makes the vinyl group electrophilic, allowing it to be used as a pharmacophore for binding to the thiol of cysteine residues.^[5] This same reactive nature is responsible for their major industrial use in vinyl sulfone dyes.^[6]

Uses

Vinyl sulfone has uses as a molluscicide pesticide.^[7]

Phenyl vinyl sulfone has been applied to ruthenium chemistry as part of olefin metathesis reactions.^[8]

Vinyl sulfone has applications to protein purification, especially when linked with mercaptoethanol.^[9]

^ Leonard, Edward C. (1970). Vinyl and Diene Monomers, Part 3. Wiley-Interscience. p. 1466.
^ Gustavson, Clarence (1952). Reactions of Phenyl Vinyl Sulfone with Organometallic Reagents. Syracuse University.
^ Keith, Lawrence H.; Walters, Douglas B. (1991). The National Toxicology Program's Chemical Data Compendium (Volume 8 ed.). CRC Press. ISBN 9780873717229.
^ Leonard, Edward C. (1970). Vinyl and Diene Monomers, Part 3. Wiley-Interscience. p. 1475.
^ Patterson, Cam; Cyr, Douglas M., eds. (2005). Ubiquitin-Proteasome Protocols. Springer Science & Business Media. p. PA7. ISBN 9781592598953.
^ Research In Technology Of Synthetic Dyes, Pigments And Intermediates. Engineers India. 2005. ISBN 9788186732519.
^ Pesticides Abstracts. U.S. Environmental Protection Agency, Office of Pesticide Programs, Program Support Division. 1975.
^ Bruneau, Christian; Dixneuf, Pierre H. (2004). Ruthenium Catalysts and Fine Chemistry. Springer Science & Business Media. ISBN 9783540205432.
^ Scopes, Robert K. (1993). Protein Purification: Principles and Practice. Springer Science & Business Media. p. 184. ISBN 9780387940724.

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