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Vinyl sulfone

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Vinyl sulfone
Identifiers
CAS Number
PubChem CID
Properties
Chemical formula C4H6O2S
Molar mass 118.15 g·mol
Appearance colorless oil
Density 1.177 g cm
Melting point -26 °C
Boiling point 90–92 °C (194–198 °F; 363–365 K) 8 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

A vinyl sulfone is an organic compound with the formula O2S(CH=CH2)2. The molecule consisting of two vinyl groups bonded to a sulfone. It is the parent of several vinyl sulfones of the type O2S(CH=CH2)R. Many vinyl sulfones are known.

Vinyl sulfones

Examples include phenyl vinyl sulfone, methyl vinyl sulfone, and ethyl vinyl sulfone.

Preparation

Divinyl sulfone is prepared from the diacetate bis(2-hydroxyethyl)sulfide. Oxidation of this diester with hydrogen peroxide gives the sulfone. The sulfone is then pyrolyzed to induce elimination of two equivalents of acetic acid:

(AcOCH2CH2)2SO2 → (CH2=CH)2SO2 + 2 HOAc (Ac = acetyl)

Other vinyl sulfones are prepared analogously to the vinyl sulfone, i.e. by H2O2-oxidation of the sulfide.

Reactions and uses

Vinyl sulfones are dienophiles. Subsequent to the cycloaddition to a vinyl sulfone, the phenylsulfonyl group can be removed by reduction with zinc.

Vinyl sulfones are a Michael acceptors. Vinyl sulfones add thiols, such as cysteine residues. This same reactive nature is responsible for their major industrial use in vinyl sulfone dyes.

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

Vinyl sulfone has applications to protein purification, especially when linked with mercaptoethanol.

Commercial applications

Vinyl sulfone has uses as a molluscicide pesticide.

Safety

Like similar compounds, vinyl sulfone is a lacrymator and skin irritant. These properties are somewhat mitigated because of its low volatility.

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. Overberger, C. G.; Schoene, D. L.; Kamath, P. M.; Tashlick, Irving (1954). "A Convenient Synthesis of Vinyl Sulfone". The Journal of Organic Chemistry. 19 (9): 1486–1489. doi:10.1021/jo01374a012.
  6. Leo A. Paquette and Richard V. C. Carr (1986). "Phenyl Vinyl Sulfone and Sulfoxide". Organic Syntheses. 64: 157. doi:10.15227/orgsyn.064.0157.
  7. Ho-shen Lin and Leo A. Paquette (1989). "Reductive Annulation of Vinyl Sulfones: Bicyclo[4.3.0.]Non-1-En-4-One". Organic Syntheses. 67: 163. doi:10.15227/orgsyn.067.0163.
  8. ^ Lucchi, Ottorino; Fabbri, Davide; Santoyo-Gonzalez, Francisco; Hernandez-Mateo, Fernando; Lopez-Jaramillo, F. Javier; Ortega-Muñoz, Mariano (2021). "Divinyl Sulfone". Encyclopedia of Reagents for Organic Synthesis. pp. 1–8. doi:10.1002/047084289X.rd476.pub2. ISBN 978-0-471-93623-7.
  9. Patterson, Cam; Cyr, Douglas M., eds. (2005). Ubiquitin-Proteasome Protocols. Springer Science & Business Media. p. PA7. ISBN 9781592598953.
  10. Research In Technology Of Synthetic Dyes, Pigments And Intermediates. Engineers India. 2005. ISBN 9788186732519.
  11. Bruneau, Christian; Dixneuf, Pierre H. (2004). Ruthenium Catalysts and Fine Chemistry. Springer Science & Business Media. ISBN 9783540205432.
  12. Scopes, Robert K. (1993). Protein Purification: Principles and Practice. Springer Science & Business Media. p. 184. ISBN 9780387940724.
  13. Pesticides Abstracts. U.S. Environmental Protection Agency, Office of Pesticide Programs, Program Support Division. 1975.


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