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Reactions of (-)-sparteine with alkali metal HMDS complexes: conventional meets the unconventional.

Reactions of (-)-sparteine with alkali metal HMDS complexes: conventional meets the unconventional.

Chemical communications (Cambridge, England) (2009-09-30)

Natalie M Clark, Pablo García-Alvarez, Alan R Kennedy, Charles T O'Hara, Gemma M Robertson

ABSTRACT

'Conventional' (-)-sparteine adducts of lithium and sodium 1,1,1,3,3,3-hexamethyldisilazide (HMDS) were prepared and characterised, along with an unexpected and 'unconventional' hydroxyl-incorporated sodium sodiate, [(-)-sparteine x Na(mu-HMDS)Na x (-)-sparteine](+)[Na(4)(mu-HMDS)(4)(OH)](-)--the complex anion of which is the first inverse crown ether anion.

MATERIALS

Product Number

Brand

Product Description

Sigma-Aldrich

Tris[N,N-bis(trimethylsilyl)amide]yttrium

Sigma-Aldrich

Tris[N,N-bis(trimethylsilyl)amide]samarium(III), 98%

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide, 97%

Sigma-Aldrich

Potassium bis(trimethylsilyl)amide solution, 1 M in THF

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution, 1 M in toluene

Sigma-Aldrich

Hexamethyldisilazane, ReagentPlus^®, 99.9%

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution, 1.0 M in hexanes

Sigma-Aldrich

Potassium bis(trimethylsilyl)amide, 95%

Sigma-Aldrich

Potassium bis(trimethylsilyl)amide solution, 0.5 M in toluene

Sigma-Aldrich

Sodium bis(trimethylsilyl)amide, 95%

Sigma-Aldrich

Sodium bis(trimethylsilyl)amide solution, 0.6 M in toluene

Sigma-Aldrich

Hexamethyldisilazane, produced by Wacker Chemie AG, Burghausen, Germany, ≥97.0% (GC)

Sigma-Aldrich

Sodium bis(trimethylsilyl)amide solution, 40% in THF

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution, 1 M in tert-butyl methyl ether

Supelco

Hexamethyldisilazane, for GC derivatization, LiChropur^™, ≥99.0% (GC)

Sigma-Aldrich

Sodium bis(trimethylsilyl)amide solution, 1.0 M in THF

Sigma-Aldrich

Hexamethyldisilazane, reagent grade, ≥99%

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution, 1.0 M in THF

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution, 1.5 M in THF

Sigma-Aldrich

Potassium bis(trimethylsilyl)amide solution, 1.0 M in 2-methyltetrahydrofuran

Sigma-Aldrich

Lithium bis(trimethylsilyl)amide solution, 0.5 M in 2-methyltetrahydrofuran