Organolithium compounds

thumb|Glass bottles containing butyllithium '''n-Butyllithium C4H9Li (abbreviated n-BuLi''') is an organolithium reagent. It is widely used as a polymerization initiator in the production of elastomers such as polybutadiene or styrene-butadiene-styrene (SBS). Also, it is broadly employed as a strong base (superbase) in the synthesis of organic compounds, such as in the pharmaceutical industry.

organometallic compound with a direct bond between a carbon and a lithium atom

chemical compound

'''tert-Butyllithium' is a chemical compound with the formula (CH3)3CLi. As an organolithium compound, it has applications in organic synthesis since it is a strong base, capable of deprotonating many carbon molecules, including benzene. tert''-Butyllithium is available commercially as solutions in hydrocarbons (such as pentane); it is not usually prepared in the laboratory.

Methyllithium is the simplest organolithium reagent, with the empirical formula LiCH3. This s-block organometallic compound adopts an oligomeric structure both in solution and in the solid state. This highly reactive compound, invariably used in solution with an ether as the solvent, is a reagent in organic synthesis as well as organometallic chemistry. Operations involving methyllithium require anhydrous conditions, because the compound is highly reactive towards water. Oxygen and carbon dioxide are also incompatible with MeLi. Methyllithium is usually not prepared, but purchased as a solutio

Phenyllithium is an organometallic agent with the empirical formula . It is most commonly used as a metalating agent in organic syntheses and a substitute for Grignard reagents for introducing phenyl groups in organic syntheses. Crystalline phenyllithium is colorless; however, solutions of phenyllithium are various shades of brown or red depending on the solvent used and the impurities present in the solute.

chemical compound

'''sec-Butyllithium' is an organometallic compound with the formula CH3CHLiCH2CH3, abbreviated sec-BuLi or s-BuLi. This chiral organolithium reagent is used as a source of sec''-butyl carbanion in organic synthesis.

chemical compound

class of chemical compounds

L-selectride is a organoboron compound with the chemical formula . A colorless salt, it is usually dispensed as a solution in THF. As a particularly basic and bulky borohydride, it is used for stereoselective reduction of ketones to alcohols. == Use in synthesis == Like other borohydrides, reductions are effected in two steps: delivery of the hydride equivalent to give the lithium alkoxide followed by hydrolytic workup:

chemical compound

lithium salt of a fatty acid

'''n-Hexyllithium, C6H13Li, sometimes abbreviated to HxLi or NHL''', is an organolithium compound used in organic synthesis as a strong base or as a lithiation reagent. It is usually encountered as a colorless or pale yellow solution in hexanes. Such solutions are highly sensitive to air and can ignite when treated with water.

chemical compound

Propynyllithium is an organolithium compound with the chemical formula . It is a white solid that is soluble in 1,2-dimethoxyethane, and tetrahydrofuran. To preclude its degradation by oxygen and water, propynyllithium and its solutions are handled under inert gas (argon or nitrogen). Although commonly depicted as a monomer, propynyllithium adopts a more complicated cluster structure as seen for many other organolithium compounds.

Hemolithin (sometimes confused with the similar space polymer hemoglycin) is a proposed protein containing iron and lithium, of extraterrestrial origin, according to an unpublished preprint. The result has not been published in any peer-reviewed scientific journal. The protein was purportedly found inside two CV3 meteorites, Allende and Acfer-086, by a team of scientists led by Harvard University biochemist Julie McGeoch. The report of the discovery was met with some skepticism and suggestions that the researchers had extrapolated too far from incomplete data.

chemical compound

Neopentyllithium is an organolithium compound with the chemical formula C5H11Li. Commercially available, it is a strong, non-nucleophilic base sometimes encountered in organometallic chemistry.

chemical compound

Vinyllithium is an organolithium compound with the formula LiC2H3. A colorless or white solid, it is encountered mainly as a solution in tetrahydrofuran (THF). It is a reagent in synthesis of organic compounds, especially for vinylations.