References
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- Brown , H. C. and Basawaiah , O. 1983 . J. Org. Chem. , 48 : 5080
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- A white suspension of ethynlymagenesium bromide intetrahydrofuran (40ml, 20mmol) was added dropwise to a stirread mixture solution of alkylselenium mono-and tribromide at -20°C in tetrahydrofuran (30ml, 20mmol) over 1h, the reaction mixture was stirred at the same temperature for an additional 0.5h. The mixture was then allowed to warm to room temperature, stirred for 1h. The mixture was treated with sat. aq NH4Cl(15ml). The phase was separated, dried (MgSO4), and concentrated in vacuo. To the residue was then added pentane (30ml) and NaBH4(0. 11g, 3mmol), respectively. The reaction mixture was stirred at room temperture for 2h. The mixture was treated with sat. aq Na2CO3(10ml). The organic phase was separated, dried over MgSO4. Removal of solvent under reduced pressure gave the terminal alkylselenoacetylene 1 which was purified by flash chromatography (light petroleum, bp30–60°C)
- Brown , H. C. and Campbell , J. B. 1980 . J. Org. Chem. , 45 : 552
- Zweifel , G. , Arzoumanian , H. and Whitney , C. C. 1967 . J. am. Chem. Soc. , 89 : 3652
- Brown , H. C. , Knights , E. and Scouten , C. 1974 . J. Amer. Chem. Soc. , 96 : 7765