CLEAR YELLOW TO BROWN LIQUID
bp 140–142 °C; d 1.442 g cm?3.
(Iodomethyl)trimethylsilane can be used as electrophile for the preparation of allylsilanes and propargylsilanes;
forms carbon alkylation adducts useful for alkene
synthesis; alkylation adducts are frequently a source of fluorideinduced
reactive intermediates, forming nitrogen and sulfur
alkylation adducts that function as ylide precursors; readily undergoes
metal–halogen exchange to generate a reagent for Peterson
methylenation.
(Iodomethyl)trimethylsilane is used for the N-alkylation of amides, in a reaction sequence to prepare unstabilized ylides for [2+3]-cycloadditions. It can react with acetoacetic acid ethyl ester to get 3-trimethylsilanyl-proπonic acid ethyl ester.
If slightly violet in colour, wash it with aqueous 1% sodium metabisulfite, H2O, dry (Na2SO4) it and fractionally distil it at 760mm. [Whitmore & Sommer J Am Chem Soc 68 481 1946, Beilstein 4 IV 3878.]
