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This species, usually called NaHMDS (sodium hexamethyldisilazide), is a strong base used for deprotonation reactions or base-catalyzed reactions. Its advantages are that it is commercially available as a solid and it is soluble not only in ethers, such as THF or diethyl ether , but also in aromatic solvents, like benzene and toluene by virtue ...
2[((CH 3) 3 Si) 2 N] 2 S + 2SCl 2 + 2SO 2 Cl 2 → S 4 N 4 + 8 (CH 3) 3 SiCl + 2SO 2 Tetraselenium tetranitride , Se 4 N 4 , is a compound analogous to tetrasulfur tetranitride and can be synthesized by the reaction of selenium tetrachloride with [((CH
Bis(trimethylsilyl)amine is synthesized by treatment of trimethylsilyl chloride with ammonia: [3] 2 (CH 3) 3 SiCl + 3 NH 3 → [(CH 3) 3 Si] 2 NH + 2 NH 4 Cl. Ammonium nitrate together with triethylamine can be used instead. [4] This method is also useful for 15 N isotopic enrichment of HMDS.
The alkali metal amides, MNH 2 (M = Li, Na, K) are commercially available. Sodium amide (also known as sodamide) is synthesized from sodium metal and ammonia with ferric nitrate catalyst. [3] [4] The sodium compound is white, but the presence of metallic iron turns the commercial material gray. 2 Na + 2 NH 3 → 2 NaNH 2 + H 2
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Tris(trimethylsilyl)amine is obtained by reaction of the sodium salt of hexamethyldisilazane - from hexamethyldisilazane and sodium amide [7] or from hexamethyldisilazane, sodium and styrene [1] - with trimethylchlorosilane in 80% yield. [8]
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 methylsilyl groups give KHMDS good solubility in most organic solvents. Solution structures are either solvated monomers or dimers (or mixtures thereof) with this depending on the coordinating power, concentration, and temperature of the solvent. [3]