Organolithium reagent

Organolithium compounds contain a direct bond between a carbon atom and a lithium atom. They are an important class of organometallic compound. The bonding between the carbon and lithium is highly polar due to the difference in electronegativity between these atoms, which effectively makes the carbon negatively charged and capable of acting as a strong base or nucleophile. These compounds are similar to Grignard reagents, but are much more reactive. Organolithium reagents such as butyllithium are widely commercially available. Due to their highly reactive nature, they must be handled under a protective atmosphere such as nitrogen or argon as they will catch fire in air.

Organolithium Reagent Media

Glass bottles containing butyllithium
A sec-butyllithium aggregate in which each of the four sec-butyl groups is associated with one face of the tetrahedron formed from four lithium atoms
Delocalized electron density in allyllithium reagents
Tetrahedron and octahedron metal cores formed by aggregation of the Li3 triangle - carbanion coordinate complex
LDA dimer with THF coordinated to Li cations
Anionic polymerization of styrene initiated by sec-BuLi
Intramolecular carbolithiation'
LiClO4 increase selectivity of t BuLi
Li add to adamantone
Li add to weinreb

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