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LiHMDS is often used in organic chemistry as a strong non-nucleophilic base. [3] Its conjugate acid has a pK a of ~26, [4] making it is less basic than other lithium bases, such as LDA (pK a of conjugate acid ~36).
The structures of common lithium amides, such as lithium diisopropylamide (LDA) and lithium hexamethyldisilazide (LiHMDS) have been extensively studied by Collum and coworkers using NMR spectroscopy. [17] Another important class of reagents is silyllithiums, extensively used in the synthesis of organometallic complexes and polysilane dendrimers.
Lithium, sodium, and potassium bis(trimethylsilyl)amides are commercially available. When free of solvent, the lithium [5] and sodium [6] complexes are trimeric, and ...
The lithium amides are more common and more soluble than the other alkali metal analogs. Potassium amides are prepared by transmetallation of lithium amides with potassium t-butoxide (see also Schlosser base ) or by reaction of the amine with potassium , potassium hydride , n-butylpotassium , or benzylpotassium .
Bis(trimethylsilyl)amine (also known as hexamethyldisilazane and HMDS) is an organosilicon compound with the molecular formula [(CH 3) 3 Si] 2 NH. The molecule is a derivative of ammonia with trimethylsilyl groups in place of two hydrogen atoms.
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: ROH + NEt 3 → RO − + H−NEt + 3; RO − + Cl−SiMe 3 → RO−SiMe 3 + Cl −; Bis(trimethylsilyl)acetamide, a popular reagent for silylation
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Bis(trimethylsilyl)acetamide (BSA) is an organosilicon compound with the formula MeC(OSiMe 3)NSiMe 3 (Me = CH 3). It is a colorless liquid that is soluble in diverse organic solvents, but reacts rapidly with moisture and solvents containing OH and NH groups .