Vinyl sulfone

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Vinyl sulfone
Divinylsulfone.svg
Identifiers
PubChem CID
Properties
C4H6O2S
Molar mass 118.15 g·mol−1
Appearancecolorless 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).

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.

Contents

Vinyl sulfones

Examples include phenyl vinyl sulfone, [2] methyl vinyl sulfone, [3] and ethyl vinyl sulfone. [4]

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: [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

Vinyl 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 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

Vinyl sulfone has uses as a molluscicide pesticide. [13]

Safety

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

Related Research Articles

<span class="mw-page-title-main">Organic sulfide</span> Organic compound with an –S– group

In organic chemistry, a sulfide or thioether is an organosulfur functional group with the connectivity R−S−R' as shown on right. Like many other sulfur-containing compounds, volatile sulfides have foul odors. A sulfide is similar to an ether except that it contains a sulfur atom in place of the oxygen. The grouping of oxygen and sulfur in the periodic table suggests that the chemical properties of ethers and sulfides are somewhat similar, though the extent to which this is true in practice varies depending on the application.

Cyclohexa-1,3-diene is an organic compound with the formula (C2H4)(CH)4. It is a colorless, flammable liquid. Its refractive index is 1.475 (20 °C, D). It is one of two isomers of cyclohexadiene, the other being 1,4-cyclohexadiene.

<span class="mw-page-title-main">Anisole</span> Organic compound (CH₃OC₆H₅) also named methoxybenzene

Anisole, or methoxybenzene, is an organic compound with the formula CH3OC6H5. It is a colorless liquid with a smell reminiscent of anise seed, and in fact many of its derivatives are found in natural and artificial fragrances. The compound is mainly made synthetically and is a precursor to other synthetic compounds. Structurally, it is an ether with a methyl and phenyl group attached. Anisole is a standard reagent of both practical and pedagogical value.

In organic chemistry, ozonolysis is an organic reaction where the unsaturated bonds are cleaved with ozone. Multiple carbon–carbon bond are replaced by carbonyl groups, such as aldehydes, ketones, and carboxylic acids. The reaction is predominantly applied to alkenes, but alkynes and azo compounds are also susceptible to cleavage. The outcome of the reaction depends on the type of multiple bond being oxidized and the work-up conditions.

<span class="mw-page-title-main">Sulfone</span> Organosulfur compound of the form >S(=O)2

In organic chemistry, a sulfone is a organosulfur compound containing a sulfonyl functional group attached to two carbon atoms. The central hexavalent sulfur atom is double-bonded to each of two oxygen atoms and has a single bond to each of two carbon atoms, usually in two separate hydrocarbon substituents.

<span class="mw-page-title-main">Sulfoxide</span> Organic compound containing a sulfinyl group (>SO)

In organic chemistry, a sulfoxide, also called a sulphoxide, is an organosulfur compound containing a sulfinyl functional group attached to two carbon atoms. It is a polar functional group. Sulfoxides are oxidized derivatives of sulfides. Examples of important sulfoxides are alliin, a precursor to the compound that gives freshly crushed garlic its aroma, and dimethyl sulfoxide (DMSO), a common solvent.

<span class="mw-page-title-main">Potassium peroxymonosulfate</span> Chemical compound

Potassium peroxymonosulfate is widely used as an oxidizing agent, for example, in pools and spas. It is the potassium salt of peroxymonosulfuric acid. Potassium peroxymonosulfate per se is rarely encountered. It is often confused with the triple salt 2KHSO5·KHSO4·K2SO4, known as Oxone.

The Ramberg–Bäcklund reaction is an organic reaction converting an α-halo sulfone into an alkene in presence of a base with extrusion of sulfur dioxide. The reaction is named after the two Swedish chemists Ludwig Ramberg and Birger Bäcklund. The carbanion formed by deprotonation gives an unstable episulfone that decomposes with elimination of sulfur dioxide. This elimination step is considered to be a concerted cheletropic extrusion.

<span class="mw-page-title-main">Diphenyl disulfide</span> Chemical compound

Diphenyl disulfide is the chemical compound with the formula (C6H5S)2. This colorless crystalline material is often abbreviated Ph2S2. It is one of the more commonly encountered organic disulfides in organic synthesis. Minor contamination by thiophenol is responsible for the disagreeable odour associated with this compound.

<span class="mw-page-title-main">Piperylene</span> Hydrocarbon compound (CH3−CH=CH−CH=CH2)

Piperylene or 1,3-pentadiene is an organic compound with the formula CH3−CH=CH−CH=CH2. It is a volatile, flammable hydrocarbon. It is one of the five positional isomers of pentadiene.

<span class="mw-page-title-main">Trimethyltin chloride</span> Chemical compound

Trimethyltin chloride is an organotin compound with the formula (CH3)3SnCl. It is a white solid that is highly toxic and malodorous. It is susceptible to hydrolysis.

<span class="mw-page-title-main">Sulfenyl chloride</span> Chemical group (R–S–Cl)

In organosulfur chemistry, a sulfenyl chloride is a functional group with the connectivity R−S−Cl, where R is alkyl or aryl. Sulfenyl chlorides are reactive compounds that behave as sources of RS+. They are used in the formation of RS−N and RS−O bonds. According to IUPAC nomenclature they are named as alkyl thiohypochlorites, i.e. esters of thiohypochlorous acid.

In nitrile reduction a nitrile is reduced to either an amine or an aldehyde with a suitable chemical reagent.

Amide reduction is a reaction in organic synthesis where an amide is reduced to either an amine or an aldehyde functional group.

2-Cyclopentenone is the organic compound with the chemical formula (CH2)2(CH)2CO. 2-Cyclopentenone contains two functional groups, a ketone and an alkene. It is a colorless liquid. Its isomer, 3-cyclopentenone is less commonly encountered.

<span class="mw-page-title-main">Thioanisole</span> Chemical compound

Thioanisole is an organic compound with the formula CH3SC6H5. It is a colorless liquid that is soluble in organic solvents. It is the simplest alkyl–aryl thioether. The name indicates that this compound is the sulfur analogue—the thioether rather than the oxygen-centered ether—of anisole.

<span class="mw-page-title-main">Transition-metal allyl complex</span>

Transition-metal allyl complexes are coordination complexes with allyl and its derivatives as ligands. Allyl is the radical with the connectivity CH2CHCH2, although as a ligand it is usually viewed as an allyl anion CH2=CH−CH2, which is usually described as two equivalent resonance structures.

Divinyl sulfide is the organosulfur compound with the formula S(CH=CH2)2. A colorless liquid with a faint odor, it is found in some species of Allium.

In organic chemistry, vinylation is the process of attaching a vinyl group to a substrate. Many organic compounds contain vinyl groups, so the process has attracted significant interest, especially since the reaction scope includes substituted vinyl groups. The reactions can be classified according to the source of the vinyl group.

In organic chemistry, methylenation is a chemical reaction that inserts a methylene group into a chemical compound:

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. 1 2 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.