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.[1] Many vinyl sulfones are known.
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| Identifiers | |
|---|---|
PubChem CID
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| Properties | |
| C4H6O2S | |
| Molar mass | 118.15 g·mol−1 |
| Appearance | colorless oil |
| Density | 1.177 g cm−3 |
| 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 [77 °F], 100 kPa).
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Vinyl sulfones
editExamples include phenyl vinyl sulfone,[2] methyl vinyl sulfone,[3] and ethyl vinyl sulfone.[4]
Preparation
editDivinyl 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 the sulfide.[6]
Reactions and uses
editVinyl sulfones are dienophiles. Subsequent to the cycloaddition to a vinyl sulfone, the phenylsulfonyl group can be removed by reduction with zinc.[7]
Vinyl sulfones are a Michael acceptors.[8] Vinyl sulfones add thiols, such as cysteine residues.[9] This same reactive nature is responsible for their major industrial use in vinyl sulfone dyes.[10]
Phenyl vinyl sulfone has been applied to ruthenium chemistry as part of olefin metathesis reactions.[11]
Vinyl sulfone has applications to protein purification, especially when linked with mercaptoethanol.[12]
Commercial applications
editVinyl sulfone has uses as a molluscicide pesticide.[13]
Safety
editLike similar compounds, vinyl sulfone is a lacrymator and skin irritant. These properties are somewhat mitigated because of its low volatility.[8]
References
edit- ^ Leonard, Edward C. (1970). Vinyl and Diene Monomers, Part 3. Wiley-Interscience. p. 1466.
- ^ Gustavson, Clarence (1952). Reactions of Phenyl Vinyl Sulfone with Organometallic Reagents. Syracuse University.
- ^ Keith, Lawrence H.; Walters, Douglas B. (1991). The National Toxicology Program's Chemical Data Compendium (Volume 8 ed.). CRC Press. ISBN 9780873717229.
- ^ Leonard, Edward C. (1970). Vinyl and Diene Monomers, Part 3. Wiley-Interscience. p. 1475.
- ^ 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.
- ^ Leo A. Paquette and Richard V. C. Carr (1986). "Phenyl Vinyl Sulfone and Sulfoxide". Organic Syntheses. 64: 157. doi:10.15227/orgsyn.064.0157.
- ^ 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.
- ^ a b 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.
- ^ Patterson, Cam; Cyr, Douglas M., eds. (2005). Ubiquitin-Proteasome Protocols. Springer Science & Business Media. p. PA7. ISBN 9781592598953.
- ^ Research In Technology Of Synthetic Dyes, Pigments And Intermediates. Engineers India. 2005. ISBN 9788186732519.
- ^ Bruneau, Christian; Dixneuf, Pierre H. (2004). Ruthenium Catalysts and Fine Chemistry. Springer Science & Business Media. ISBN 9783540205432.
- ^ Scopes, Robert K. (1993). Protein Purification: Principles and Practice. Springer Science & Business Media. p. 184. ISBN 9780387940724.
- ^ Pesticides Abstracts. U.S. Environmental Protection Agency, Office of Pesticide Programs, Program Support Division. 1975.
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