Lithium tert-butoxide explained

Lithium tert-butoxide is the metalorganic compound with the formula LiOC(CH₃)₃. A white solid, it is used as a strong base in organic synthesis. The compound is often depicted as a salt, and it often behaves as such, but it is not ionized in solution. Both octameric^[1] and hexameric forms have been characterized by X-ray crystallography^[2]

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.^[3]

Reactions

As a strong base, lithium tert-butoxide is easily protonated.

Lithium tert-butoxide is used to prepare other tert-butoxide compounds such as copper(I) t-butoxide and hexa(tert-butoxy)dimolybdenum(III):^[4]

2 MoCl₃(thf)₃ + 6 LiOBu-t → Mo₂(OBu-t)₆ + 6 LiCl + 6 thf

Related compounds

• Sodium tert-butoxide
• Potassium tert-butoxide

Notes and References

1. 10.1002/1521-3749(200209)628:9/10<2067::AID-ZAAC2067>3.0.CO;2-N. Kristall- und Molekülstrukturen von Lithium- und Natrium-tert-butoxid. 2002. Nekola. Henning. Olbrich. Falk. Behrens. Ulrich. Zeitschrift für Anorganische und Allgemeine Chemie. 628. 9–10. 2067–2070.
2. 10.1021/ja038420m. Characterization of a Kinetically Stable, Highly Ordered, Octameric Form of Lithiumtert-Butoxide and Its Implications Regarding Aggregate Formation. 2004. Allan. John F.. Nassar. Roger. Specht. Elizabeth. Beatty. Alicia. Calin. Nathalie. Henderson. Kenneth W.. Journal of the American Chemical Society. 126. 2. 484–485. 14719943.
3. 10.15227/orgsyn.051.0096. Esterification Of Hindered Alcohols: tert-Butyl p-Toluate. Organic Syntheses. 1971. 51. 96. G. P.. Crowther. E. M.. Kaiser. R. A.. Woodruff. C. R.. Hauser.
4. Book: 10.1002/9781118744994.ch18. Dimolybdenum and Ditungsten Hexa(Alkoxides). Inorganic Syntheses. 36. 2014. Broderick. Erin M.. Browne. Samuel C.. Johnson. Marc J. A.. 95–102. 9781118744994.