3.1.2.2 Reactions with Epoxides
Epoxides react with organolithium reagents to give primary alcohols (as in the case of Grignard reagents) (Scheme 10). In general, the organolithium attacks the epoxides at the less sterically hindered carbon, as with any nucleophile.
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Scheme 10 |
3.1.2.3 Reactions with Carbon Dioxide
A major difference between the reactivity of organomagnesium halide and organolithium reagent is observed in their reactivity towards CO2. The reaction of organomagnesium halide with CO2 stops at the carboxylate stage, while in case of organolithium reagents, the carboxylate ion formed reacts with another equiv of organolithium to generate a ketone (Scheme 11).
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Scheme 11 |
3.1.2.4 Reactions with Aryl Cyanides
As in the case of organomagnesium halides, the reactions of organolithium reagents with aryl cyanides give imine salts, which undergo hydrolysis in the presence of water to give ketones (Scheme 12).
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Scheme 12 |
3.1.2.5 Electrophilic Displacement
Reaction of an organic halide with an organometallic compound is known as metal-halogen exchange reaction is example for electrophilic displacement. This reaction is useful for the synthesis of vinyl- and phenyl lithium (Scheme 13).
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Scheme 13 |
3.1.2.6 Nucleophilic Displacement
Reactions of alkyl and aryl halides can be reacted with alkyl and aryl lithium reagents to give hydrocarbons. The reaction of alkyl halides with alkyl lithium takes place by SN2 mechanism. While aryl halides react with aryl lithum via addition-elimination process (Scheme 14).
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