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Sodium bis(trimethylsilyl)amide is the chemical compound with the formula ((CH3)3Si)2NNa. This species, usually called NaHMDS (sodium hexamethyldisilazide), is a strong base used for deprotonation reactions or base catalyzed reaction. Its advantages are that it is available as a solid and it is soluble in a wide range of nonpolar solvents by virtue of the lipophilic TMS groups.
Additional recommended knowledge
It is common that polar organometallic reagents are depicted as ions, when in fact such species are rarely ionic. The structure shown in the figure is a better representation - the sodium atom is attached to the nitrogen atom via a polar covalent bond.
Applications in synthesis
NaHMDS is widely used as a base for C-H acids. Typical reactions:
NaHMDS is also used as a base for N-H acids.
NaHMDS reacts with alkyl halides to give amine derivatives:
This method has been extended to aminomethylation via the reagent (CH3)3Si)2NCH2OMe, which contains a displacable methoxy group.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Sodium_bis(trimethylsilyl)amide". A list of authors is available in Wikipedia.|