Lithium bis(trimethylsilyl)amide
Lithium bis(trimethylsilyl)amide is a lithiated organosilicon compound. Its chemical formula is LiN(SiMe3)2. It is commonly abbreviated as LiHMDS which means lithium hexamethyldisilazide. It is mainly used as a strong non-nucleophilic base and as a ligand.
Preparation
It can be made by the deprotonation of bis(trimethylsilyl)amine with n-butyllithium.[1] Once its made, the compound can be purified by sublimation or distillation.
Uses
It is often used in organic chemistry as a strong non-nucleophilic base.[2] It can be used to make many organolithium compounds, including acetylides or lithium enolates.[2][3]
Lithium Bis(trimethylsilyl)amide Media
In situ formation then reaction of w:LiHMDS with w:Benzylideneacetone to produce an enolate. See Danheiser, R. L.; Miller, R. F.; Brisbois, R. G. (1990), "Detrifluoroacetylative Diazo Group Transfer: (E)-1-Diazo-4-phenyl-3-buten-2-one", Org. Synth. 73: 134,
The aggregation of lithium bis(trimethylsilyl)amide (LiHMDS) into dimers, trimers and higher oligomers
- LiHMDS-tmeda complex.png
structure of LiHMDS-tmeda complex
- Li2(Sitms2)2(THF)2.png
crystallographically determined structure of Li2[N(Sitms2])2(THF)2
- The real "Li N(Sitms2 )2".png
crystallographically determined structure of "Li[N(Sitms2])2"
References
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- ↑ 2.0 2.1 Lua error in Module:Citation/CS1/Identifiers at line 630: attempt to index field 'known_free_doi_registrants_t' (a nil value).
- ↑ Lua error in Module:Citation/CS1/Identifiers at line 630: attempt to index field 'known_free_doi_registrants_t' (a nil value).
