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Concept
Methyllithium
Summary
Methyllithium is the simplest organolithium reagent with the empirical formula CH3Li. This s-block organometallic compound adopts an oligomeric structure both in solution and in the solid state. This highly reactive compound, invariably used in solution with an ether as the solvent, is a reagent in organic synthesis as well as organometallic chemistry. Operations involving methyllithium require anhydrous conditions, because the compound is highly reactive toward water. Oxygen and carbon dioxide are also incompatible with MeLi. Methyllithium is usually not prepared, but purchased as a solution in various ethers.
In the direct synthesis, methyl bromide is treated with a suspension of lithium in diethyl ether.
2 Li + MeBr → LiMe + LiBr
The lithium bromide forms a complex with the methyllithium. Most commercially available methyllithium consists of this complex. "Halide-free" methyllithium is prepared from methyl chloride. Lithium chloride precipitates from the diethyl ether since it does not form a strong complex with methyllithium. The filtrate consists of fairly pure methyllithium. Alternatively, commercial methyllithium can be treated with dioxane to precipitate LiBr(dioxane), which can be removed by filtration. The use of halide-free vs LiBr-MeLi has a decisive effect on some syntheses.
Methyllithium is both strongly basic and highly nucleophilic due to the partial negative charge on carbon and is therefore particularly reactive towards electron acceptors and proton donors. In contrast to n-BuLi, MeLi reacts only very slowly with THF at room temperature, and solutions in ether are indefinitely stable. Water and alcohols react violently. Most reactions involving methyllithium are conducted below room temperature. Although MeLi can be used for deprotonations, n-butyllithium is more commonly employed since it is less expensive and more reactive.
Methyllithium is mainly used as the synthetic equivalent of the methyl anion synthon.
Official source
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