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Lithium ''tert''-butoxide is the metalloorganic compound with the formula LiOC(CH3)3. A white solid, it is used as a strong base in
Lithium ''tert''-butoxide is commercially available as a solution and as a solid, but it is often generated ''in situ'' for laboratory use because samples are so sensitive and older samples are often of poor quality. It can be obtained by treating tert-butanol with butyl lithium.
organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...
. The compound is often depicted as a salt, and it often behaves as such, but it is not ionized in solution. Both octameric and hexameric forms have been characterized by X-ray crystallography
X-ray crystallography is the experimental science determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to diffract into many specific directions. By measuring the angles ...
Preparation
Lithium ''tert''-butoxide is commercially available as a solution and as a solid, but it is often generated ''in situ'' for laboratory use because samples are so sensitive and older samples are often of poor quality. It can be obtained by treating tert-butanol with butyl lithium.
Reactions
As a strong base, lithium ''tert''-butoxide is easily protonated. Lithium ''tert''-butoxide is used to prepare other ''tert''-butoxide compounds such ascopper(I) t-butoxide
Copper(I) ''t''-butoxide is an alkoxide of copper(I). It is a white sublimable solid. It is a reagent in the synthesis of other copper compounds.
The compound was originally obtained by salt metathesis from lithium tert-butoxide and copper(I) ch ...
and hexa(tert-butoxy)dimolybdenum(III)
Hexa(''tert''-butoxy)dimolybdenum(III) is a coordination complex of molybdenum(III). It is one of the homoleptic alkoxides of molybdenum. An orange, air-sensitive solid, the complex has attracted academic attention as the precursor to many organ ...
:
:2 MoCl3(thf)3 + 6 LiOBu-t → Mo2(OBu-t)6 + 6 LiCl + 6 thf
Related compounds
*Sodium tert-butoxide
Sodium ''tert''-butoxide is the chemical compound with the formula (CH3)3CONa. It is a strong base and a non-nucleophilic base. It is flammable and moisture sensitive. It is sometimes written in chemical literature as sodium ''t''-butoxide. It ...
*Potassium tert-butoxide
Potassium ''tert''-butoxide is the chemical compound with the formula K+(CH3)3CO−. This colourless solid is a strong base (pKa of conjugate acid around 17), which is useful in organic synthesis. It exists as a tetrameric cubane-type cluster ...
References
{{Lithium compounds Alkoxides Lithium compounds Non-nucleophilic bases Organolithium compounds Reagents for organic chemistry Tert-butyl compounds