Allyltrimethylsilane

Allyltrimethylsilane (Trimethyl-prop-2-enylsilane) is an organosilicon compound. Allyltrimethylsilane undergoes photochemical thiol-ene reactions with thiolated soybean oil. Allyltrimethylsilane participates in carbon-carbon bond formation via allylation reactions with acetals, ketals, aldehydes and ketones, forms cyclopropane through reaction with aldehydes, and reacts with iodine to produce trimethylsilyl iodide. Allyltrimethylsilane is applicable to research related to organic synthesis^[1][2][3]. In Vitro:Allyltrimethylsilane undergoes a photochemical thiol-ene reaction with thiolated soybean oil to form a liquid, inert silicon-containing adduct, and no oligomerization occurs during the synthesis process^[1].
Allyltrimethylsilane exhibits differential reaction outcomes under different Lewis acid catalytic systems: it reacts with triethyl orthoformate to produce diallyl ether instead of homoallyl acetal; under the action of various catalysts such as liquid SO₂, I₂, TMSNTf₂, BiBr₃, FeCl₃, and Al‑MCM‑41, it reacts with various acetals/ketals to afford homoallyl ethers with yields ranging from variable to quantitative, as well as C‑allyl glycoside products with an α/β stereoselectivity of 8/1; it also reacts with aliphatic aldehydes and aromatic aldehydes to yield homoallyl alcohols^[2].

Allyltrimethylsilane can be synthesized from allylmagnesium bromide and trimethylchlorosilane; it undergoes Markovnikov-selective electrophilic addition with hydrogen bromide, hydrogen iodide, and chlorine; it yields n-propyltrimethylsilane via catalytic hydrogenation with Raney nickel; its reaction with anhydrous aluminum chloride initiates non-simple polymerization, producing viscous polymers with a high boiling range^[3].