N-methyl-N-triethylsilylmethanamine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Triethylchlorosilane, 75.4 g (0.5 mole), was added dropwise to a solution of 73 ml (1.1 mole) of dimethylamine in 500 ml diethyl ether at 10°-20°. A precipitate was removed by filtration, and the resulting filtrate distilled to provide 64.8 g of dimethylaminotriethylsilane as a colorless liquid, bp 88° (46 mm). A 47.8 g (0.3 mole) sample of the silane was added dropwise to a solution of 5 ml (0.09 mole) of sulfur tetrafluoride in 100 ml of ether cooled to -70°. The resulting mixture was allowed to warm to about 23° and stirred for one week. The resulting white solid precipitate was collected on a filter, washed with ether, and dried under nitrogen to give 6.8 g of tris(dimethylamino)sulfonium bifluoride as colorless crystals: mp 117°-120°; 19F NMR (CD3CN) δ-150.4 ppm; 1H NMR (CD3CN) δ+2.95 ppm. A precipitate was removed by filtration the resulting filtrate distilled

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Triethylchlorosilane, 75.4 g (0.5 mole), was added dropwise to a solution of 73 ml (1.1 mole) of dimethylamine in 500 ml diethyl ether at 10°-20°. A precipitate was removed by filtration, and the resulting filtrate distilled to provide 64.8 g of dimethylaminotriethylsilane as a colorless liquid, bp 88° (46 mm). A 47.8 g (0.3 mole) sample of the silane was added dropwise to a solution of 5 ml (0.09 mole) of sulfur tetrafluoride in 100 ml of ether cooled to -70°. The resulting mixture was allowed to warm to about 23° and stirred for one week. The resulting white solid precipitate was collected on a filter, washed with ether, and dried under nitrogen to give 6.8 g of tris(dimethylamino)sulfonium bifluoride as colorless crystals: mp 117°-120°; 19F NMR (CD3CN) δ-150.4 ppm; 1H NMR (CD3CN) δ+2.95 ppm. A precipitate was removed by filtration the resulting filtrate distilled