Chemical Properties
Triphenylsilane is an off-white solid that is soluble in most organic solvents. It is used in certain cases for the preparation of triphenylsilyl ethers, which serve as alcohol-protecting groups. The triphenylsilyl group is considerably more stable (about 400 times) than the TMS group toward acidic hydrolysis.
Uses
Triphenylsilane acts as a reactant or reagent for catalytic hydrogen deuterium exchange reactions of silanes, to be oxidized by carbon nanotube-gold nanohybrids, for hydrolysis by ruthenium complexes, for hydrosilylation to produce enolsilanes, for synthesis of bromosilanes, for ozone oxidation of silyl-alkenes for synthesis of α-O-silylated acyloin derivatives. It is used to synthesize hydrido silyl and bis(silyl) bis(imidazolinylidene) nickel complexes.
Uses
Triphenylsilane(789-25-3) is reducing agent for esters, xanthates, and polychloroalkanes;
protecting group for alcohols. It takes part in the reactions of Deoxygenations, Hydrosilylations, Lewis Acid-assisted Hydrosilylations, Heteroatom Reductions, Multiple Bond Reductions, Alkene Hydrogenations, Silylations, etc.
Application
More effective radical-based reagent for reduction of
organic halides than the trialkylsilanes. Compares
well with tri-n-butyltin hydride in reduction of enones to
ketones. Shows good selectivity in the reduction of cyclic
hemiacetals. Converts O-acetyl furanoses and pyranoses
to deoxy sugars.
Preparation
Triphenylsilane(789-25-3) can be synthesized by reducing phenylsilane (PhSiH3) with a reducing agent such as lithium aluminum hydride (LiAlH4). The overall reaction equation is as follows:
3 PhSiH3 + 2 LiAlH4 → C18H16Si + 2 LiH + 2 AlH3
This reaction is typically carried out in anhydrous conditions and under inert gas atmosphere.
Purification Methods
Purify it by recrystallisation from MeOH. [Gilman & Zuech J Am Chem Soc 81 5925 1959, Westermark Acta Chem Scand 9 947 1955, IR: Kaplan J Am Chem Soc 76 5880 1954, Beilstein 16 II 605, 16 III 1199, 16 IV 1369.]
