IODOMETHYLTRIMETHYLSILANE

Hydrolytic Sensitivity

3: reacts with aqueous base

Review of synthetic utility.¹
Employed in silyl-methylation of alkynes.²
Converts aldehydes, ketones, ?,?-enones to silyl enol ethers.³
Intermediate for allylic silane synthon, 2-(trimethylsilyl)ethyltriphenylphosphonium ^{iodide.4
Useful for the introduction of the trimethylsilylmethyl group.5}

1. Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis, Fuchs, P. L. Ed., John Wiley and Sons, Ltd., 2011, p. 323-336.
2. Schmid, R. et al. J. Am. Chem. Soc. 1980, 102, 5122.
3. Cazeau, P. et al. Tetrahedron 1987, 43, 2075, 2089.
4. Fleming, I. et al. Synthesis 1979, 446.
5. Vedejs, E. J. Org. Chem. 1985, 50, 2170.

Packaging Under

Nitrogen