Metalation of hydrocarbons

The rate of hydrogen exchange depends on the protolytic properties of both the solvent and the substrate. In fact there is a correspondence between the magnitude of the rate constants for deuterium exchange with ND3 and the conventional ionization constants of hydrocarbons which were used by Conant and Wheland (1932) and by McEwen (1936) to obtain the first quantitative estimates of the acidity of hydrocarbons. To do this, they determined the equilibrium of metallation of hydrocarbons by organo-alkali metal compounds. This reaction was described by Shorygin (1910) and is represented by the equation... 

The metallation of hydrocarbons with the lutetium complex [(Me5C5)2LuH]2 (Scheme V.l.) may be regarded as an evidence for the high reactivity of REM organohydrides [17]. 

Similar considerations apply to the degenerate lithium-hydrogen exchange reactions across the entire first row of the periodic table, including the reaction of methane with methyllithium. The latter reaction is a model for the metalations of hydrocarbons by alkyllithiums. This type of reaction was modeled for substituted benzenes and toluenes by reaction with lithium hydride ... 

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