Divinyl sulfide explained

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]

Notes and References

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