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Sodium ''tert''-butoxide is the
Sodium tert-butoxide is used to prepare tert-butoxide complexes. For example
, , 
, -
, hexamer, , nonamer
chemical compound
A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one ele ...
with the formula (CH3)3CONa. It is a strong base and a non-nucleophilic base
As the name suggests, a non-nucleophilic base is a sterically hindered organic base that is a poor nucleophile. Normal bases are also nucleophiles, but often chemists seek the proton-removing ability of a base without any other functions. Typica ...
. It is flammable and moisture sensitive. It is sometimes written in 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
Sodium hydride is the chemical compound with the empirical formula Na H. This alkali metal hydride is primarily used as a strong yet combustible base in organic synthesis. NaH is a saline (salt-like) hydride, composed of Na+ and H− ions, in ...
.
Reactions
One application for sodium ''tert''-butoxide is as a non-nucleophilic base. It has been widely used in theBuchwald–Hartwig amination
In organic chemistry, the Buchwald–Hartwig amination is a chemical reaction for the synthesis of carbon–nitrogen bonds via the palladium-catalyzed coupling reactions of amines with aryl halides. Although Pd-catalyzed C-N couplings were repo ...
, as in this typical example:
Sodium tert-butoxide is used to prepare tert-butoxide complexes. For example hexa(tert-butoxy)ditungsten(III)
Hexa(''tert''-butoxy)ditungsten(III) is a coordination complex of tungsten(III). It is one of the homoleptic alkoxides of tungsten. A red, air-sensitive solid, the complex has attracted academic attention as the precursor to many organotungsten ...
is thus converted 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. {, class="wikitable" style="text-align:center;" ,, ,
, -
, hexamer, , nonamer
Related compounds
*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. ...
* Lithium tert-butoxide
References