Divinyl sulfide

Divinyl sulfide

Names
Preferred IUPAC name (Ethenylsulfanyl)ethene
Other names vinyl sulfide, DVS
Identifiers
CAS Number	627-51-0  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:177668
ChemSpider	11817
PubChem CID	12321
UNII	CL87X0NVJA
CompTox Dashboard (EPA)	DTXSID10211766
InChI InChI=1S/C4H6S/c1-3-5-4-2/h3-4H,1-2H2 Key: UIYCHXAGWOYNNA-UHFFFAOYSA-N
SMILES C=CSC=C
Properties
Chemical formula	C4H6S
Molar mass	86.15 g·mol−1
Appearance	colorless liquid
Density	0.9098 g/cm3 (20 °C)
Melting point	20 °C (68 °F; 293 K)
Boiling point	84 °C (183 °F; 357 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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 . ^[1]

Preparation

Divinyl sulfide is formed from hydrogen sulfide and acetylene. ^[2] Divinylsulfide can arise when inadvertently when acetylene is generated by hydrolysis of technical-grade calcium carbide contaminated with calcium sulfide. ^[3]

Divinylsulfide was first prepared in 1920 by the reaction of bis(2-chloroethyl)sulfide with sodium ethoxide: ^[3]

(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. ^[4] One example is phenyl vinyl sulfide. ^{[5] [6]} Alkyl ketones react with thiols in the presence of phosphorus pentoxide to give vinyl sulfides: ^[7]

RSH + CH₃C(O)R' → CH₂=C(SR)R' + H₂O

References

1. "Divinyl sulfide (FDB012121)". FooDB.
2. Trotuş, Ioan-Teodor; Zimmermann, Tobias; Schüth, Ferdi (2014). "Catalytic Reactions of Acetylene: A Feedstock for the Chemical Industry Revisited". Chemical Reviews. 114 (3): 1761–1782. doi: 10.1021/cr400357r . PMID   24228942.
3. Boris A. Trofimov; S. V. Amosova (1984). "Divinyl Sulfide: Synthesis, Properties, and Applications". Sulfur Reports. 3 (9): 323–393. doi:10.1080/01961778408082463.
4. Nina A. Nedolya; Boris A. Trofimov (1994). "Sulfur-Containing Vinyl Ethers". Sulfur Reports. 15 (2): 237–316. doi:10.1080/01961779408048961.
5. Leo A. Paquette; Richard V. C. Carr (1986). "Phenyl Vinyl Sulfone and Sulfoxide". Organic Syntheses. 64: 157. doi:10.15227/orgsyn.064.0157.
6. Daniel S. Reno; Richard J. Pariza (1997). "Phenyl Vinyl Sulfide". Organic Syntheses. 74: 124. doi:10.15227/orgsyn.074.0124.
7. Trost, Barry M.; Lavoie, Alvin C. (1983). "Enol thioethers as enol substitutes. An alkylation sequence". Journal of the American Chemical Society. 105 (15): 5075–5090. doi:10.1021/ja00353a037.