(Trimethylsilyl)methyllithium

It crystallizes as the hexagonal prismatic hexamer [LiCH2TMS]6, akin to some polymorphs of methyllithium.

[2] Many adducts have been characterized including the diethyl ether complexed cubane [Li4(μ3-CH2TMS)4(Et2O)2][3] and [Li2(μ-CH2TMS)2(TMEDA)2].

It is prepared by the Grignard reaction of (trimethylsilyl)methyl chloride.

Such complexes are usually produced by salt metathesis involving metal chlorides.

These compounds are often highly soluble in nonpolar organic solvents, enjoying stability due to their steric bulk and resistance to beta-hydride elimination.

Structure of the organoscandium complex with two (trimethylsilyl)methyl ligands, (C 5 H 5 )Sc(CH 2 TMS) 2 (THF). [ 8 ] Color scheme: O (red), Sc (blue), Si (orange).