Organolithium chemistry
Organolithium chemistry is the science of organolithium compounds describing their physical properties, synthesis, and reactions. Organolithium compounds in organometallic chemistry contain carbon-lithium chemical bonds. A major subset and perhaps the most used organolithium compounds are organolithium reagents, such as butyllithium
Classification
Alkyl and aryl monolithium compounds
Various depictions of the methyl lithium tetramer. Colour code: Li- purple C- black H- whiteAlkyl and aryl monolithium are illustrated by their simplest members, methyl lithium and phenyl lithium. These useful reagents have complicated structures owing to the tendency of the C-Li unit to aggregate, forming clusters. These compounds are prepared by metal-halogen exchange, which entails stirring solutions of the alkyl halide with lithium metal:
Lithium-reduced polycyclic aromatics
Naphthalene, anthracene, and related polycyclic aromatic compounds are reduced by lithium to give Li+ salts of their radical anions:Lithium naphthalene is used as a reductant in the synthesis of organic, organometallic, and inorganic chemistry.
Dilithio compounds
These compounds, which have two C-Li bonds can be classified into two distinct groups. Simplest but rare is dilithiomethanide and its many derivatives. Some derivatives have even been characterized by X-ray crystallography.The more common dilithiated organic compounds the Li atoms are bound to separate carbon atoms. 1,4-dilithiobutane would be an example.
Dilithioacetylide.