Tris(trimethylsilyl)methane explained

Tris(trimethylsilyl)methane is the organosilicon compound with the formula (tms)₃CH (where tms = (CH₃)₃Si). It is a colorless liquid that is highly soluble in hydrocarbon solvents.

Trisyl chemistry

Reaction of tris(trimethylsilyl)methane with methyl lithium gives tris(trimethylsilyl)methyllithium, called trisyllithium:

(tms)₃CH + CH₃Li → (tms)₃CLi + CH₄Trisyllithium is useful in Petersen olefination reactions:^[1]

(tms)₃CLi + R₂CO → (tms)₂C=CR₂ + tmsOLi

Trisyllithium is also a source of the bulky trisyl ligand. Some tris(trimethylsilyl)methyl derivatives are far more stable than less substituted derivatives. For example, is a well-behaved tellurol.^[2] is a rare example of a robust organothallium(I) compound.^[3]

See also

• Tris(trimethylsilyl)silane

References

1. Encyclopedia: 10.1002/047084289X.rt417. Tris(trimethylsilyl)methane. Encyclopedia of Reagents for Organic Synthesis. 2001. Sakurai. Hideki. 0-471-93623-5 .
2. Sadekov ID, Zakharov AV. 1999. Stable tellurols and their metal derivatives. Russ. Chem. Rev.. 68. 11. 909–923. 10.1070/rc1999v068n11abeh000544. 1999RuCRv..68..909S. 250864006 .
3. 10.1002/anie.199700641 . Tl^I[C(SiMe₃)₃]—An Alkylthallium(I) Compound with a Distorted Tetrahedron of Tl Atoms in the Solid State . 1997 . Angewandte Chemie International Edition in English . 36 . 1–2 . 64–65 . Uhl W, Keimling SU, Klinkhammer KW, Schwarz W .