Organosodium compounds with halides

Organosodium compounds are prepared from sodium and other organometallic compounds or active methylene compounds by reaction with organic halides, cleavage of ethers, or addition to unsaturated compounds. Some aromatic vinyl compounds and allyhc compounds also give sodium derivatives. 

Organosodium compounds can, in principle, be prepared by the same methods as the corresponding lithium compounds. However, reaction of organic halides (usually chlorides) with metallic sodium in an inert solvent has been introduced recently ... 

According to Hugel and Lerer324 the organosodium compounds obtained from polycyclic aromatic compounds such as naphthalene and anthracene in liquid ammonia or other media also react with alkyl halides, and especially with isopentyl and isobutyl chloride they yield doubly substituted hydrocarbons. The experimental conditions are briefly illustrated as follows ... 

Closely related to the Wurtz reaction is the synthesis of organosodium compounds, such as amylsodium (25) and phenylsodium (13). These can be prepared from sodium and the organic halide by using an excess of sodium and keeping the temperature low in order to minimize the Wurtz reaction. The promising alfin catalyst for the polymerization of butadiene is prepared by a reaction of this type (24). The catalyst consists essentially of allylsodium, mixed with sodium chloride and a sodium alkoxide. 

A variety of organometallic compoundshave been used to couple with alkyl halides. " Organosodium and organopotassium compounds are more reactive than Grignard reagents and couple even with less reactive halides. Organolithium... 

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