divinyl sulfide
{{Chembox
| ImageFile = Divinyl sulfide.svg
| ImageSize =
| ImageAlt =
| PIN = (Ethenylsulfanyl)ethene
| OtherNames = vinyl sulfide, DVS
|Section1={{Chembox Identifiers
| CASNo = 627-51-0
| CASNo_Ref = {{Cascite|correct|CAS}}
| ChEBI = 177668
| ChemSpiderID = 11817
| PubChem = 12321
| UNII = CL87X0NVJA
| StdInChI=1S/C4H6S/c1-3-5-4-2/h3-4H,1-2H2
| StdInChIKey = UIYCHXAGWOYNNA-UHFFFAOYSA-N
| SMILES = C=CSC=C
}}
|Section2={{Chembox Properties
| C=4|H=6|S=1
| MolarMass =
| Appearance = colorless liquid
| Density = 0.9098 g/cm3 (20 °C)
| MeltingPtC = 20
| BoilingPtC = 84
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
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.{{cite web | work = FooDB | url = http://foodb.ca/compounds/FDB012121 | title = Divinyl sulfide (FDB012121)}}
Preparation
Divinyl sulfide is formed from hydrogen sulfide and acetylene.{{cite journal |doi=10.1021/cr400357r |title=Catalytic Reactions of Acetylene: A Feedstock for the Chemical Industry Revisited |date=2014 |last1=Trotuş |first1=Ioan-Teodor |last2=Zimmermann |first2=Tobias |last3=Schüth |first3=Ferdi |journal=Chemical Reviews |volume=114 |issue=3 |pages=1761–1782 |pmid=24228942 |doi-access=free }} Divinylsulfide can arise when inadvertently when acetylene is generated by hydrolysis of technical-grade calcium carbide contaminated with calcium sulfide.{{cite journal|journal=Sulfur Reports|volume=3|issue=9|year=1984|title=Divinyl Sulfide: Synthesis, Properties, and Applications|author=Boris A. Trofimov |author2=S. V. Amosova |pages=323–393|doi=10.1080/01961778408082463}}
Divinylsulfide was first prepared in 1920 by the reaction of bis(2-chloroethyl)sulfide with sodium ethoxide:
:(ClCH2CH2)2S + 2 NaOEt → (CH2=CH)2S + 2 EtOH + 2 NaCl
Monovinyl sulfides
With the formula CH2=CHSR, a variety of monovinyl sulfides are known. They can arise by the dehydrohalogenation of -2-haloethyl phenyl sulfides.{{cite journal|title=Sulfur-Containing Vinyl Ethers|author=Nina A. Nedolya |author2=Boris A. Trofimov |journal=Sulfur Reports|year=1994|volume=15|issue=2|pages=237–316|doi=10.1080/01961779408048961}} One example is phenyl vinyl sulfide.{{cite journal |doi=10.15227/orgsyn.064.0157|title=Phenyl Vinyl Sulfone and Sulfoxide|author=Leo A. Paquette |author2=Richard V. C. Carr|journal=Organic Syntheses |year=1986 |volume=64 |page=157 }}{{cite journal |doi=10.15227/orgsyn.074.0124|title=Phenyl Vinyl Sulfide |journal=Organic Syntheses |year=1997 |volume=74 |page=124|author=Daniel S. Reno |author2=Richard J. Pariza}} Alkyl ketones react with thiols in the presence of phosphorus pentoxide to give vinyl sulfides:{{cite journal |doi=10.1021/ja00353a037 |title=Enol thioethers as enol substitutes. An alkylation sequence |date=1983 |last1=Trost |first1=Barry M. |last2=Lavoie |first2=Alvin C. |journal=Journal of the American Chemical Society |volume=105 |issue=15 |pages=5075–5090 }}
:{{chem2|RSH + CH3C(O)R' -> CH2\dC(SR)R' + H2O}}