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]

Vinyl sulfone functional group ("R" is an arbitrary structure)

The sulfone makes the vinyl group electrophilic, allowing it to be used as a pharmacophore for binding to the thiol of threonine 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]

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