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When attached to certain functional groups in a reactant molecule, trimethylsilyl groups may also be used as temporary protecting groups during chemical synthesis or some other chemical reactions. In chromatography, derivitization of accessible silanol groups in a bonded stationary phase with trimethylsilyl groups is referred to as endcapping.
TMSCl is reactive toward nucleophiles, resulting in the replacement of the chloride. In a characteristic reaction of TMSCl, the nucleophile is water, resulting in hydrolysis to give the hexamethyldisiloxane: + + The related reaction of trimethylsilyl chloride with alcohols can be exploited to produce anhydrous solutions of hydrochloric acid in alcohols, which find use in the mild synthesis of ...
The most important esters with common protecting-group use are the acetate, benzoate, and pivalate esters, for these exhibit differential removal. Sterically hindered esters are less susceptible to nucleophilic attack: Chloroacetyl > acetyl > benzoyl > pivaloyl Trimethylsilyl chloride, activated with imidazole, protects a secondary alcohol
The protection mechanism begins with the base deprotonating the alcohol group. Next, the deprotonated alcohol group attacks the silyl atom of the silyl halide compound. The halide acts as a leaving group and ends up in solution. A workup step follows to remove any excess base within the solution. The overall reaction scheme is as follows:
Trimethylsilylacetylene is commercially available. It may also be prepared in a manner similar to other silyl compounds: deprotonation of acetylene with a Grignard reagent, followed by reaction with trimethylsilyl chloride. [4] Trimethylsilylacetylene is a precursor to 1,4-bis(trimethylsilyl)buta-1,3-diyne, a protected form of 1,3-butadiyne. [5]
The methylchlorosilanes react with water to produce hydrogen chloride, giving siloxanes. In the case of trimethylsilyl chloride, the hydrolyzed product is hexamethyldisiloxane: 2 ((CH 3) 3 SiCl + H 2 O → [(CH 3) 3 Si] 2 O + 2 HCl. The analogous reaction of dimethyldichlorosilane gives siloxane polymers or rings: n (CH 3) 2 SiCl 2 + n H 2 O ...
tert-Butyldimethylsilyl chloride is an organosilicon compound with the formula (Me 3 C)Me 2 SiCl (Me = CH 3). It is commonly abbreviated as TBSCl or TBDMSCl. It is a chlorosilane containing two methyl groups and a tert-butyl group. As such it is more bulky that trimethylsilyl chloride. It is a colorless or white solid that is soluble in many ...
The conversion of the aldehyde group to a diether “head” occurs in two steps. The first step involves addition of ethylene glycol and trimethylsilyl chloride (TMSCl) in CH 2 Cl 2 solvent. Addition of TBAF in THF solvent removes the silyl protecting group. [1]