Divinyl sulfide

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Divinyl sulfide
Divinyl sulfide.svg
Names
Preferred IUPAC name
(Ethenylsulfanyl)ethene
Other names
vinyl sulfide, DVS
Identifiers
3D model (JSmol)
UNII
  • InChI=1S/C4H6S/c1-3-5-4-2/h3-4H,1-2H2
    Key: UIYCHXAGWOYNNA-UHFFFAOYSA-N
  • C=CSC=C
Properties
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).

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][2]

It is notable as the product from hydrogen sulfide and acetylene, a combination that arises when acetylene is generated by hydrolysis of technical-grade calcium carbide, which contains impurities of 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[edit]

With the formula CH2=CHSR, a variety of monovinyl sulfides are known. They often arise by the dehydrohalogenation of -2-haloethyl phenyl sulfides.[4] One example is phenyl vinyl sulfide.[5][6]

References[edit]

  1. ^ Ruigh, William L.; Major, Randolph T. (1931). "The Preparation and Properties of Pure Divinyl Ether". Journal of the American Chemical Society. 53 (7): 2662–2671. doi:10.1021/ja01358a030.
  2. ^ "Divinyl sulfide (FDB012121)". FooDB.
  3. ^ a b Boris A. Trofimov, S. V. Amosova (1984). "Divinyl Sulfide: Synthesis, Properties, and Applications". Sulfur Reports. 3 (9): 323–393. doi:10.1080/01961778408082463.{{cite journal}}: CS1 maint: uses authors parameter (link)
  4. ^ Nina A. Nedolya, Boris A. Trofimov (1994). "Sulfur-Containing Vinyl Ethers". Sulfur Reports. 15 (2): 237–316. doi:10.1080/01961779408048961.{{cite journal}}: CS1 maint: uses authors parameter (link)
  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.