Lithium hexamethyldisilazide (source code)

= Lithium hexamethyldisilazide

<Lithium hexamethyldisilazide> is the <lithium> <salt> of $\mathrm{N(SiMe_3)_2^-}$, a bulky <amide> anion. It is used as a strong <base> for transformations such as <enolate> formation.

The <lithium> ion can coordinate <oxygen> donors and organize aggregates. Consequently, calling the reagent non-nucleophilic is a useful comparison under specified conditions, not a claim that it cannot participate in any competing reaction.

https://doi.org/10.1021/jacs.7b05057[Primary enolization study: aggregation, solvent and E-Z selectivity; supporting NMR and rate measurements]{ref}