Lithium tetramethylpiperidide
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, to favor elimination reactions.
 | |
| Names | |
|---|---|
| IUPAC name
Lithium tetramethylpiperidide | |
| Systematic IUPAC name
1-Lithio-2,2,6,6-tetramethylpiperidine | |
| Identifiers | |
3D model (JSmol) |
|
| ChemSpider | |
| ECHA InfoCard | 100.209.926 |
PubChem CID |
|
CompTox Dashboard (EPA) |
|
| |
| |
| 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). | |
  | |
| Infobox references | |
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]
gollark: You *can* give that money away, though.
gollark: ↑
gollark: Not in an "actively doing evil" sense, but arguably that's just a matter of where you set some arbitrary zero point.
gollark: For example, I do not really donate money to charity, despite at least having theoretically nonzero money. I feel somewhat guilty about this if I think about it very hard.
gollark: Distributing punishment based on that would make things like advertisements for charities horrible infohazards.
See also
References
- amide primer H. J. Reich 2002
- 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.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.