Vinyl sulfone explained

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]

Notes and References

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