Formula C9H18LiN | ||
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Lithium tetramethylpiperidide (often abbreviated LiTMP or LTMP) 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.
Contents
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 commercially available as such.
Structure
Like many lithium reagents it has a tendency to aggregate, forming a tetramer in the solid state.
References
Lithium tetramethylpiperidide Wikipedia(Text) CC BY-SA