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. 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

References


LITHIUM TETRAPHENYLBORATE TRIS(1,2DIMETHOXYETHANE) 75965354 wiki

Figure 7 from Lithium 2,2,6,6TetramethylpiperidideMediated α and β

Figure 1 from Effects of lithium salts on the stereochemistry of ketone

Table 1 from Lithium 2,2,6,6TetramethylpiperidideMediated α and β

Figure 4 from Concealed cyclotrimeric polymorph of lithium 2,2,6,6