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OrganoMetallurgy/Drafts/Tris(trimethylsilyl)methyl lithium
Names
	Other names Trisyl lithium, lithium tris(trimethylsilyl)methanide
Identifiers
CAS Number	28830-22-0;
ChemSpider	25935425;
PubChem CID	10889992;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tris(trimethylsilyl)methyllithium is a reagent used to introduce the extremely bulky tris(trimethylsilyl)methyl (trisyl) ligand or functional group on to compounds/molecules.

Structure

The crystal stucture of the tetrahydrofuran adduct consists of [Li(thf)₄]⁺ cations and [Li{C(SiMe₃)₃}₂]^– anions.^[1]

Synthesis/Preparation

Tris(trimethylsilyl)methyllithium can be prepared by the lithiation of tris(trimethylsilyl)methane by methyllithium in a mixture of tetrahydrofuran and diethyl ether.^[2]

Reactions

References

^ Eaborn, Colin; Hitchcock, Peter B.; Smith, J. David; Sullivan, Alice C. (1983-01-01). "Crystal structure of the tetrahydrofuran adduct of tris(trimethylsilyl)-methyl-lithium, [Li(thf)4][Li{C(SiMe3)3}2], an ate derivative of lithium". Journal of the Chemical Society, Chemical Communications. 0 (15). doi:10.1039/c39830000827. ISSN 0022-4936.
^ Sakurai, Hideki (2001). Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, Ltd. doi:10.1002/047084289x.rt417. ISBN 9780470842898.

Category:Silanes Category:Organolithium compounds

[1] Eaborn, Colin; Hitchcock, Peter B.; Smith, J. David; Sullivan, Alice C. (1983-01-01). "Crystal structure of the tetrahydrofuran adduct of tris(trimethylsilyl)-methyl-lithium, [Li(thf)4][Li{C(SiMe3)3}2], an ate derivative of lithium". Journal of the Chemical Society, Chemical Communications. 0 (15). doi:10.1039/c39830000827. ISSN 0022-4936.

[2] Sakurai, Hideki (2001). Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, Ltd. doi:10.1002/047084289x.rt417. ISBN 9780470842898.

[1]

[2]