Sodium tert-butoxide


Sodium tert-butoxide is a chemical compound with the formula 3CONa. 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.

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:

Structure

Sodium tert-butoxide forms clusters in the solid state, both hexamers and nonamers.
hexamernonamer

Related compounds