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| Names | |
|---|---|
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Preferred IUPAC name
(Ethenylsulfanyl)ethene | |
| Other names
vinyl sulfide, DVS
| |
| Identifiers | |
3D model (
JSmol)
|
|
| ChEBI | |
| ChemSpider | |
PubChem
CID
|
|
| UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
| 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]
Preparation
Divinyl sulfide is formed from hydrogen sulfide and acetylene. [2] Divinylsulfide can arise when inadvertantly 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
- ^ "Divinyl sulfide (FDB012121)". FooDB.
- ^ 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.
- ^ 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.
- ^ Nina A. Nedolya; Boris A. Trofimov (1994). "Sulfur-Containing Vinyl Ethers". Sulfur Reports. 15 (2): 237–316. doi: 10.1080/01961779408048961.
- ^ Leo A. Paquette; Richard V. C. Carr (1986). "Phenyl Vinyl Sulfone and Sulfoxide". Organic Syntheses. 64: 157. doi: 10.15227/orgsyn.064.0157.
- ^ Daniel S. Reno; Richard J. Pariza (1997). "Phenyl Vinyl Sulfide". Organic Syntheses. 74: 124. doi: 10.15227/orgsyn.074.0124.
- ^ 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.
|
| |
| Names | |
|---|---|
|
Preferred IUPAC name
(Ethenylsulfanyl)ethene | |
| Other names
vinyl sulfide, DVS
| |
| Identifiers | |
3D model (
JSmol)
|
|
| ChEBI | |
| ChemSpider | |
PubChem
CID
|
|
| UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
| 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]
Preparation
Divinyl sulfide is formed from hydrogen sulfide and acetylene. [2] Divinylsulfide can arise when inadvertantly 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
- ^ "Divinyl sulfide (FDB012121)". FooDB.
- ^ 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.
- ^ 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.
- ^ Nina A. Nedolya; Boris A. Trofimov (1994). "Sulfur-Containing Vinyl Ethers". Sulfur Reports. 15 (2): 237–316. doi: 10.1080/01961779408048961.
- ^ Leo A. Paquette; Richard V. C. Carr (1986). "Phenyl Vinyl Sulfone and Sulfoxide". Organic Syntheses. 64: 157. doi: 10.15227/orgsyn.064.0157.
- ^ Daniel S. Reno; Richard J. Pariza (1997). "Phenyl Vinyl Sulfide". Organic Syntheses. 74: 124. doi: 10.15227/orgsyn.074.0124.
- ^ 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.