Vinyl sulfone

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Vinyl sulfone functional group ("R" is an arbitrary structure) Vinylsulfone Group.svg
Vinyl sulfone functional group ("R" is an arbitrary structure)

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]

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Vinyl sulfone dyes are reactive dyes comprising a vinyl sulfone group as reactive group (a fiber-bonding site of the reactive dye, "reactive hook"). Due to the relatively high reactivity of the vinyl sulfone group with water (residual moisture, air humidity), it is present in many commercial products in a protected form. For protection, an ethylsulfonyl group is substituted with a leaving group. During the dyeing process under alkaline conditions, the vinyl sulfone group is released by an elimination reaction:


Formation of the vinyl sulfone group by alkaline elimination. R= alkyl or aryl radical, X=-OSO3H, -Cl

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.