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Hexamethyldisilane

Hexamethyldisilane (TMS<sub>2</sub>) is the organosilicon compound with the formula Si<sub>2</sub>(CH<sub>3</sub>)<sub>6</sub>, abbreviated Si<sub>2</sub>Me<sub>6</sub>. It is a colourless liquid, soluble in organic solvents.

Synthesis and reactions

Hexamethyldisilane can be produced by Wurtz-like coupling of trimethylsilyl chloride in the presence of a reducing agent such as potassium graphite:

With an excess of the reductant, the alkali metal silyl derivative is produced:

The Si-Si bond in hexamethyldisilane is cleaved by strong nucleophiles and electrophiles. Alkyl lithium compounds react as follows:

Si<sub>2</sub>Me<sub>6</sub> + RLi → RSiMe<sub>3</sub> + LiSiMe<sub>3</sub>

Iodine gives trimethylsilyl iodide.

Me<sub>3</sub>Si&minus;SiMe<sub>3</sub> + I<sub>2</sub> → 2 SiMe<sub>3</sub>I

References