Lithium tetramethylpiperidide

Lithium tetramethylpiperidide is a chemical compound with the molecular formula. It is used as a non-nucleophilic base, being comparable to LiHMDS in terms of steric hindrance.

Synthesis

It is synthesised by the deprotonation of 2,2,6,6-tetramethylpiperidine with n-butyllithium, this is typically performed at −78 °C, although there are reports of it being performed at 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.