Lithium tetramethylpiperidide (often abbreviated LiTMP or LTMP) is a chemical compound with the molecular formula LiC9H18N. 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.
See also Lithium diisopropylamide Lithium amide
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