Lithium tetramethylpiperidide

Lithium tetramethylpiperidide
Names
IUPAC name
Lithium tetramethylpiperidide
Systematic IUPAC name
1-Lithio-2,2,6,6-tetramethylpiperidine
Identifiers
38227-87-1 YesY
3D model (Jmol) Interactive image
Interactive image
ChemSpider 21428984 YesY
ECHA InfoCard 100.209.926
PubChem 11051814
Properties
C9H18LiN
Molar mass 147.19 g·mol−1
Acidity (pKa) 37
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.

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 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

  1. amide primer H. J. Reich 2002
  2. M.F. Lappert, M.J. Slade, A. Singh, J.L. Atwood, R.D. Rogers and 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.
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