Trimethylsulfoxonium iodide

Trimethylsulfoxonium iodide
IUPAC name

S,S,S-Trimethylsulfoxonium iodide
Other names

Trimethylsulphoxonium iodide; Trimethyloxosulfonium iodide
Identifiers
CAS number 1774-47-6
Jmol-3D images Image 1
Properties
Molecular formula C3H9IOS
Molar mass 220.07 g mol−1
Melting point

208-212 °C
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Trimethylsulfoxonium iodide is a sulfoxonium salt. It is used to generate dimethyloxosulfonium methylide by reaction with sodium hydride.[1] The latter compound is used as a methylene-transfer reagent, and is used to prepare epoxides.

This compound is commercially available. It may be prepared by the reaction of dimethyl sulfoxide and iodomethane:[2]

(CH3)2SO + CH3I → (CH3)3SO+I−

References

  1. ^ E. J. Corey1 and Michael Chaykovsky2., "Methylenecyclohexane Oxide", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv5p0755 ; Coll. Vol. 5: 755 
  2. ^ Lampman, Gary M.; Koops, Roger W.; Olden, Caroline C. (1985). "Phosphorus and sulfur ylide formation: Preparation of 1-benzoyl-2-phenylcyclopropane and 1,4-diphenyl-1,3-butadiene by phase transfer catalysis". J. Chem. Ed. 62 (3): 267. doi:10.1021/ed062p267.