Lithium hexamethyldisilazide
ID: lithium-hexamethyldisilazide
Lithium hexamethyldisilazide is the lithium salt of , 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.
[ref]
https://doi.org/10.1021/jacs.7b05057. Primary enolization study: aggregation, solvent and E-Z selectivity; supporting NMR and rate measurements
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