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 at −78 °C. Recent reports show that this reaction can also be performed 0 °C.1 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.2
See also
References
amide primer H. J. Reich 2002 http://www.chem.wisc.edu/areas/reich/Handouts/lireagents/amidebases.pdf ↩
M.F. Lappert; M.J. Slade; A. Singh; J.L. Atwood; R.D. Rogers; R. Shakir (1983). "Structure and reactivity of sterically hindered lithium amides and their diethyl etherates: crystal and molecular structures of [Li{N(SiMe3)2}(OEt2)]2 and tetrakis(2,2,6,6-tetramethylpiperidinatolithium)". Journal of the American Chemical Society. 105 (2): 302–304. doi:10.1021/ja00340a031. /wiki/Journal_of_the_American_Chemical_Society ↩