Sodium tert-butoxide (or sodium t-butoxide) is a chemical compound with the formula (CH3)3CONa (abbr. NaOtBu).http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=359270|ALDRICH&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC It is a strong, non-nucleophilic base. It is flammable and moisture sensitive. It is sometimes written in the chemical literature as sodium t-butoxide. It is similar in reactivity to the more common potassium tert-butoxide.
The compound can be produced by treating tert-butyl alcohol with sodium hydride.PM. Dewick, 2013. Essentials of Organic Chemistry: For Students of Pharmacy, Medicinal Chemistry and Biological Chemistry. John Wiley & Sons; p. 157.
Reactions One application for sodium tert-butoxide is as a non-nucleophilic base. It has been widely used in the Buchwald–Hartwig amination, as in this typical example:
Sodium tert-butoxide is used to prepare tert-butoxide complexes. For example hexa(tert-butoxy)ditungsten(III) is thus obtained by the salt metathesis reaction from a ditungsten heptachloride: NaW2Cl7(THF)5 + 6 NaOBu-t → W2(OBu-t)6 + 7 NaCl + 5 THF
Structure Sodium tert-butoxide forms clusters in the solid state, both hexamers and nonamers.
hexamernonamer
Related compounds Potassium tert-butoxide Lithium tert-butoxide Sodium tert-amyloxide (), a highly soluble analogue of sodium tert-butoxide
References