Lithium tetramethylpiperidide
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Structural formula of lithium tetramethylpiperidide | |
Names | |
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IUPAC name
Lithium tetramethylpiperidide
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Systematic IUPAC name
1-Lithio-2,2,6,6-tetramethylpiperidine
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Identifiers | |
38227-87-1 | |
ChemSpider | 21428984 |
Jmol 3D model | Interactive image Interactive image |
PubChem | 11051814 |
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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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verify (what is ?) | |
Infobox references | |
Lithium tetramethylpiperidide (often abbreviated LiTMP or LTMP) is an 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.[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
- ↑ amide primer H. J. Reich 2002
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