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Diphenyl sulfide is an organosulfur compound with the chemical formula (C6H5)2S, often abbreviated as Ph2S, where Ph stands for phenyl. It is a colorless liquid with an unpleasant odor. Diphenyl sulfide is an aromatic sulfide. The molecule consists of two phenyl groups attached to a sulfur atom.

Synthesis, reactions, occurrence

Many methods exist for the preparation of diphenyl sulfide. It arises by a Friedel-Crafts-like reaction of sulfur monochloride and benzene.[4]Diphenyl sulfide and its analogues can also be produced by coupling reactions using metal catalysts.[5] It can also be prepared by reduction of diphenyl sulfone.[6]

Diphenyl sulfide is a product of the photodegradation of the fungicide edifenphos.[7]

Diphenyl sulfide is a precursor to triarylsulfonium salts, which are used as photoinitiators. The compound can be oxidized to the sulfoxide with hydrogen peroxide.[8]

References

  1. ^ "3". CRC Handbook of Chemistry and Physics (90 ed.). 2010. p. 220.
  2. ^ a b "GESTIS-Stoffdatenbank".
  3. ^ "Diphenyl sulfide".
  4. ^ Hartman, W. W.; Smith, L. A.; Dickey, J. B. (1934). "Diphenyl Sulfide". Organic Syntheses. 14: 36. doi:10.15227/orgsyn.014.0036.
  5. ^ Lian, Zhong; Bhawal, Benjamin N.; Yu, Peng; Morandi, Bill (2017). "Palladium-catalyzed carbon-sulfur or carbon-phosphorus bond metathesis by reversible arylation". Science. 356 (6342): 1059–1063. Bibcode:2017Sci...356.1059L. doi:10.1126/science.aam9041. PMID 28596362. S2CID 206657928.
  6. ^ Krafft, F.; Vorster, W. (1893). "Ueber Umwandlung des Diphenylsulfons in Diphenylsulfid und Diphenylselenid". Berichte der Deutschen Chemischen Gesellschaft. 26 (3): 2813–2822. doi:10.1002/cber.18930260393.
  7. ^ Murai, Toshinobu (1977). "Photodecomposition of O -Ethyl S , S -Diphenyl Phosphorodithiolate (Edifenphos)". Agricultural and Biological Chemistry. 41: 71–77. doi:10.1080/00021369.1977.10862468.
  8. ^ Sato, Kazuhiko; Hyodo, Mamoru; Aoki, Masao; Zheng, Xiao-Qi; Noyori, Ryoji (2001). "Oxidation of Sulfides to Sulfoxides and Sulfones with 30% Hydrogen Peroxide under Organic Solvent- and Halogen-Free Conditions". Tetrahedron. 57 (13): 2469–2476. doi:10.1016/s0040-4020(01)00068-0.
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