TMEDA copper chloride

Oxidative coupling of terminal acetylenes in the presence of copper(I) catalysts is the best method of preparing symmetrically substituted butadiyne derivatives,5 and has been applied to the coupling of trimethylsilyl-acetylene. Better yields are obtained using the Hay procedure in which the catalyst is the TMEDA complex of copper(I) chloride.7 The procedure submitted here is an improved version of Walton and Waugh s synthesis of BTMSBD by the Hay coupling of trimethylsilylacetylene.2 BTMSBD has also been prepared by... 

Analysis of Reagent Purity addition of aqueous ammonium chloride gives >95% conversion to 1-trimethylsilylpropyne. Preparative Method a solution of l-lithio-3-trimethylsilyl-1-propyne containing MMlV W -tetramethylethylenediamine (TMEDA) in ether or THF is added to a slurry of copper(I) iodide in ether at —78°C, then warmed to — 10°C and used immediately. ... 

Acrylonitrile, A, A/, A/, A/ -tetramethylethylenediamine (TMEDA), triethylamine, copper(I) chloride, trichlorosilane. 

Under a nitrogen atmosphere, acrylonitrile (15.919 g, 0.300 mol), TMEDA (1.047 g, 9.01 mmol), triethylamine (0.912 g, 9.01 mmol), and copper(I) chloride (1.78 g, 18.0 mmol) were placed in a 100 mL three-necked round-bottomed flask equipped with a stir bar, a dropping funnel, a reflux condenser, and a thermometer. Trichlorosilane (44.70 g, 0.330 mol) was added dropwise to this mixture for 1 h. As an exothermic reaction took place, the dropping speed of trichlorosilane was adjusted so that the temperature of the mixture was kept below 60°C. After the addition of trichlorosilane, the mixture was stirred at room temperature for 4 h. The reaction mixture was distilled imder reduced pressure to give trichloro-2-cyanoethylsilane (52.86 g, 93%). Bp 86°C/llmmHg. The distillate solidified on standing at room temperature for several hours. 

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