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Vinyl sulfone

From Wikipedia, the free encyclopedia
Vinyl sulfone
Identifiers
Properties
C4H6O2S
Molar mass118.15 g·mol−1
Appearancecolorless oil
Density1.177 g cm−3
Melting point-26 °C
Boiling point90–92 °C (194–198 °F; 363–365 K) 8 mmHg
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Avinyl sulfone is anorganic compound with the formulaO2S(CH=CH2)2. The molecule consisting of twovinyl groups bonded to asulfone. It is the parent of several vinyl sulfones of the typeO2S(CH=CH2)R.[1] Manyvinyl sulfones are known.

Vinyl sulfones

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Examples includephenyl vinyl sulfone,[2]methyl vinyl sulfone,[3] andethyl vinyl sulfone.[4]

Preparation

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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:[5]

(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 thesulfide.[6]

Reactions and uses

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Vinyl sulfones aredienophiles. Subsequent to thecycloaddition to a vinyl sulfone, thephenylsulfonyl group can be removed by reduction with zinc.[7]

Vinyl sulfones areMichael acceptors.[8] Vinyl sulfones addthiols, such ascysteine residues.[9] This same reactive nature is responsible for their major industrial use invinyl sulfone dyes.[10]

Phenyl vinyl sulfone has been applied toruthenium chemistry as part ofolefin metathesis reactions.[11]

Vinyl sulfone has applications toprotein purification, especially when linked withmercaptoethanol.[12]

Commercial applications

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Vinyl sulfone has uses as amolluscicidepesticide.[13]

Safety

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Like similar compounds, vinyl sulfone is a lacrymator and skin irritant. These properties are somewhat mitigated because of its low volatility.[8]

References

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  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. ^abLucchi, 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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