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

• Glasbottles containing Butyllithium, Buli.jpg

  Glass bottles containing butyllithium

• Sec-butyllithium-2D-skeletal.png

  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

• Allyllithium.svg

  Delocalized electron density in allyllithium reagents

• Building block of alkyllithium aggregates.png

  Tetrahedron and octahedron metal cores formed by aggregation of the Li3 triangle - carbanion coordinate complex

• Dimerliamide.jpg

  LDA dimer with THF coordinated to Li cations

• Anionic polymerization of styrene initiated by sec-BuLi.png

  Anionic polymerization of styrene initiated by sec-BuLi

• Intramolecular carbolithiation'.png

  Intramolecular carbolithiation'

• LiClO4 increase selectivity.png

  LiClO4 increase selectivity of t BuLi

• Li add to adamantone.png

  Li add to adamantone

• Li add to weinreb.png

  Li add to weinreb