10264. Dimethylsulfoxonium Methylide

Nomenclature

CAS number: 5367-24-8
Corey's reagent; Corey-Chaykovsky reagent; dimethyloxosulfonium methylide; DMSY.
C3H8OS; mol wt 92.16.
C 39.10%, H 8.75%, O 17.36%, S 34.79%.

Description and references

Methylene transfer reagent. Prepn from trimethylsulfoxonium iodide or chloride and NaH: E. J. Corey, M. Chaykovsky, J. Am. Chem. Soc. 84, 867 (1962) DOI; and synthetic applications: eidem, ibid. 87, 1353 (1965) DOI. Alternate large scale prepn: J. S. Ng, Synth. Commun. 20, 1193 (1990) DOI. NMR characterization and physical properties: H. Schmidbaur, W. Tronich, Tetrahedron Lett. 9, 5335 (1968) DOI. Review of chemistry: Y. G. Gololobov et al., Tetrahedron 43, 2609-2651 (1987) DOI; J. S. Ng, C. Liu in Encyclopedia of Reagents for Organic Synthesis, vol. 3, L. A. Paquette, Ed. (John Wiley & Sons, Chichester, 1995) pp 2159-2165 DOI; C. Awasthi, Synlett 2008, 1423-1424 DOI.

Chemical structure

Properties

mp 9-10°. bp0.1 41-43°. Sol in THF, DMSO, 1,4-dioxane, DMF. Typically generated in situ. Stable as soln in THF for several months at 0°; decomposes after one week at room temp.

Use

Reagent in organic synthesis for epoxidation of ketones and aldehydes; cyclopropanation of α,β-unsaturated carbonyl compounds; methylation reactions.