Lithium tetramethylpiperidide
Lithium tetramethylpiperidide is a chemical compound with the molecular formula C9H18LiN. It is used as a non-nucleophilic base, being comparable to LiHMDS in terms of pKa and steric hindrance, to favor elimination reactions.Synthesis
It is synthesised by the deprotonation of 2,2,6,6-tetramethylpiperidine with n-butyllithium at −78 °C. Recent reports show that this reaction can also be performed 0 °C. The compound is stable in a THF/ethylbenzene solvent mixture and is commercially available as such.Structure
Like many lithium reagents it has a tendency to aggregate, forming a tetramer in the solid state.
