{{Chembox | ImageFile = Divinylsulfone.svg | ImageSize = 90 | ImageAlt = | IUPACName = | OtherNames = |Section1={{Chembox Identifiers | CASNo = 77-77-0 | ChEBI = 53729 | ChEMBL = 349205 | ChemSpiderID = 6251 | EC_number = 201-057-6 | Gmelin = 558721 | PubChem = 6496 | UNII = 5PFN71LP8M | UNNumber = 2810 (DIVINYL SULFONE) | StdInChI=1S/C4H6O2S/c1-3-7(5,6)4-2/h3-4H,1-2H2 | StdInChIKey = AFOSIXZFDONLBT-UHFFFAOYSA-N | SMILES = C=CS(=O)(=O)C=C }} |Section2={{Chembox Properties | C=4|H=6|O=2|S = 1 | MolarMass = | Appearance = colorless oil | Density =1.177 g cm<sup>−3</sup> | MeltingPt = -26 °C | MeltingPt_notes = | BoilingPtC = 90–92 | BoilingPt_notes = 8 mmHg | Solubility = }} |Section3={{Chembox Hazards | GHS_ref=[https://pubchem.ncbi.nlm.nih.gov/compound/6496#section=Safety-and-Hazards] | GHSPictograms = {{GHS05}}{{GHS06}}{{GHS07}}{{GHS08}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|300|310|314|315|335|341}} | PPhrases = {{P-phrases|203|260|261|262|264|264+265|270|271|280|301+316|301+330+331|302+352|302+361+354|304+340|305+354+338|316|317|318|319|321|330|332+317|361+364|362+364|363|403+233|405|501}} | MainHazards = | FlashPt = | AutoignitionPt = }} }} A '''vinyl sulfone''' is an organic compound with the formula {{chem2|O2S(CH\dCH2)2}}. The molecule consisting of two vinyl groups bonded to a sulfone. It is the parent of several vinyl sulfones of the type {{chem2|O2S(CH\dCH2)R}}.<ref name="divinyl70">{{cite book |last1=Leonard |first1=Edward C. |title=Vinyl and Diene Monomers, Part 3 |date=1970 |publisher=Wiley-Interscience |page=1466}}</ref> Many '''vinyl sulfones''' are known.

==Vinyl sulfones== Examples include phenyl vinyl sulfone,<ref name="cg52">{{cite book |last1=Gustavson |first1=Clarence |title=Reactions of Phenyl Vinyl Sulfone with Organometallic Reagents |date=1952 |publisher=Syracuse University}}</ref> methyl vinyl sulfone,<ref name="ntp585">{{cite book |last1=Keith |first1=Lawrence H. |last2=Walters |first2=Douglas B. |title=The National Toxicology Program's Chemical Data Compendium |date=1991 |publisher=CRC Press |isbn=9780873717229 |edition=Volume 8 |url=https://books.google.com/books?id=3rmiNPNOe0AC&pg=PA585}}</ref> and ethyl vinyl sulfone.<ref name="ethyl70">{{cite book |last1=Leonard |first1=Edward C. |title=Vinyl and Diene Monomers, Part 3 |date=1970 |publisher=Wiley-Interscience |page=1475}}</ref>

==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:<ref>{{cite journal |doi=10.1021/jo01374a012 |title=A Convenient Synthesis of Vinyl Sulfone |date=1954 |last1=Overberger |first1=C. G. |last2=Schoene |first2=D. L. |last3=Kamath |first3=P. M. |last4=Tashlick |first4=Irving |journal=The Journal of Organic Chemistry |volume=19 |issue=9 |pages=1486–1489 }}</ref> :{{chem2|(AcOCH2CH2)2SO2 -> (CH2\dCH)2SO2 + 2 HOAc}} (Ac = acetyl) Other vinyl sulfones are prepared analogously to the vinyl sulfone, i.e. by H<sub>2</sub>O<sub>2</sub>-oxidation of the sulfide.<ref>{{cite journal |doi=10.15227/orgsyn.064.0157|author=Leo A. Paquette and Richard V. C. Carr |title=Phenyl Vinyl Sulfone and Sulfoxide |journal=Organic Syntheses |date=1986 |volume=64 |page=157 }}</ref>

==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.<ref>{{cite journal |doi=10.15227/orgsyn.067.0163 |title=Reductive Annulation of Vinyl Sulfones: Bicyclo&#91;4.3.0.&#93;Non-1-En-4-One |journal=Organic Syntheses |date=1989 |volume=67 |page=163|author=Ho-shen Lin and Leo A. Paquette }}</ref>

Vinyl sulfones are Michael acceptors.<ref name=eros>{{cite book |doi=10.1002/047084289X.rd476.pub2 |chapter=Divinyl Sulfone |title=Encyclopedia of Reagents for Organic Synthesis |date=2021 |last1=Lucchi |first1=Ottorino |last2=Fabbri |first2=Davide |last3=Santoyo-Gonzalez |first3=Francisco |last4=Hernandez-Mateo |first4=Fernando |last5=Lopez-Jaramillo |first5=F. Javier |last6=Ortega-Muñoz |first6=Mariano |pages=1–8 |isbn=978-0-471-93623-7 }}</ref> Vinyl sulfones add thiols, such as cysteine residues.<ref name="cyr05">{{cite book |editor1-last=Patterson |editor1-first=Cam |editor2-last=Cyr |editor2-first=Douglas M. |title=Ubiquitin-Proteasome Protocols |date=2005 |publisher=Springer Science & Business Media |page=PA7 |isbn=9781592598953 |url=https://books.google.com/books?id=qv3ok4y7-j0C&pg=PA7}}</ref> This same reactive nature is responsible for their major industrial use in vinyl sulfone dyes.<ref name="eiri05">{{cite book |title=Research In Technology Of Synthetic Dyes, Pigments And Intermediates |date=2005 |publisher=Engineers India |isbn=9788186732519 |url=https://books.google.com/books?id=c98gNFmnnYAC&pg=PA274}}</ref>

Phenyl vinyl sulfone has been applied to ruthenium chemistry as part of olefin metathesis reactions.<ref name="bruneau05">{{cite book |last1=Bruneau |first1=Christian |last2=Dixneuf |first2=Pierre H. |title=Ruthenium Catalysts and Fine Chemistry |date=2004 |publisher=Springer Science & Business Media |isbn=9783540205432 |url=https://books.google.com/books?id=6UP05zXC5ioC&pg=PA101}}</ref>

Vinyl sulfone has applications to protein purification, especially when linked with mercaptoethanol.<ref name="scopes93">{{cite book |last1=Scopes |first1=Robert K. |title=Protein Purification: Principles and Practice |date=1993 |publisher=Springer Science & Business Media |page=184 |isbn=9780387940724 |url=https://books.google.com/books?id=byi_lK0gk6cC&pg=PA184}}</ref>

==Commercial applications== Vinyl sulfone has uses as a molluscicide pesticide.<ref name="epapest">{{cite book |title=Pesticides Abstracts |date=1975 |publisher=U.S. Environmental Protection Agency, Office of Pesticide Programs, Program Support Division}}</ref>

==Safety== Like similar compounds, vinyl sulfone is a lacrymator and skin irritant. These properties are somewhat mitigated because of its low volatility.<ref name=eros/>

==References== {{reflist}}

Category:Vinyl sulfones Category:Pesticides Category:Medicinal chemistry Category:Dienes

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