Lithium metal organomercurials

Alkylalkali metal compounds are also commonly formed from reactions with organomercury compounds. Solvent-free LiC(SiMe3)3 has been prepared by the reaction of an organomercuryhalide with butyl lithium in hexanes (equation 19). ... 

A different method of preparation is advisable if the pure, solvent-free organolithium compound is required. In a procedure due to Schlenk and Holtz50 the organolithium compound is prepared from metallic lithium and the organomercury compound in an indifferent solvent since most organolithium compounds, in particular the higher alkyl derivatives, are very readily soluble in hydrocarbons, they can be easily separated from the separating mercury and then obtained pure by evaporation of the solution. 

The simple organometallic compounds usually react with metals by displacement, when the more reactive can displace the less reactive metal from the compound. The most important example of this is the utilization of organomercury compounds to obtain the more reactive metal alkyls of such metals as sodium, lithium, and aluminum ... 

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