BIS[BIS(TRIMETHYLSILYL)AMINO]TIN II

Uses

Reagent for the conversion of aldehydes and ketones to N,N-dialkyleneamines.

Synthesis Reference(s)

[1]Burnell-Curty, C.; Roskamp, E. J. unpublished results. Schaeffer, C. D., Jr.; Myers, L. K.; Coley, S. M.; Otter, J. C.; Yoder, C. H. J. Chem. Educ. 1990, 67, 347.

reaction suitability

core: tin

Synthesis

BIS[BIS(TRIMETHYLSILYL)AMINO]TIN II's synthesis method: a 500 mL round bottomed flask equipped with a nitrogen inlet was charged with 65 mL of dioxane and 40.1 g of anhydrous Tin(II) Chloride (0.21 mol). This suspension was allowed to stir for 30 min at rt, and was then treated with 71.0 g of Lithium Hexamethyldisilazide (0.43 mol) in several small portions. During the addition of LiN(TMS)2 the reaction mixture became warm and turned dark red-orange in color. A Vigreux column and vacuum distillation apparutus were attached to the flask, and it was heated at 35 °C for 45 min. The apparatus was then placed under vacuum (0.5 mmHg) and the bath warmed to 85 °C. The forerun, mainly dioxane, was collected with the help of a dry ice acetone bath. Bis[N,N-bis(trimethylsilyl)amino]tin(II) distilled as a bright red oil between 105-115 °C (80.4 g, 86%); this material solidified upon standing at rt.^[1]

Precautions

BIS[BIS(TRIMETHYLSILYL)AMINO]TIN II is nonpyrophoric but should be handled under a nitrogen atmosphere, and stored in a refrigerator. Since the solid is very soluble in hexane, it is convenient to prepare a hexane solution which may then be transferred via conventional syringe techniques. It readily hydrolyzes to tin(II) oxide, which is of reputed low toxicity. Use in a fume hood.