Organosodium compounds, reactivity

In contrast with the low reactivity observed with n-butyllithium solutions in hydrocarbons (5) or ether (6), the n-butyllithium-amine adducts rapidly metalate unsaturated hydrocarbons including even simple olefins. In this respect they surpass even organosodium compounds and will probably prove to be of considerable synthetic value. Addition of a hexane solution containing equimolar amounts of n-butyllithium and an amine to excess toluene at ordinary temperatures results in rapid formation of a benzyllithium-amine complex that in some cases separates as a yellow crystalline solid. 

Which is more reactive, an organolithium compound or an organosodium compound ... 

Organosodium compounds in which the negative charge is delocalized may be obtained by a greater variety of methods. They are all brightly coloured, and their reactivity is less. They are also commonly soluble in ether, and not normally decomposed by it, the sodium ion being solvated. Only a few fairly typical examples can be given here. 

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... 

Double-bond isomerization reaction of simple olefins requires strong basic catalysts. Various catalyst systems have been reported for this reaction. They include sodium-organosodium catalysts prepared in situ by reacting an excess of sodium with a reactive organic compound, such as o-chlorotoluene or anthracene as reported by Pines and co-workers 5-8). 

All organolithium and organosodium chelates are extremely reactive toward water, oxygen, polar compounds, etc. They are almost invariably more reactive than the corresponding unchelated compounds. 

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