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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 23
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Original Articles

Regio-and Stereoselective Synthesis of (E)-1-Alkylseleno-1, 4-Pentadienes by Cross-Coupling of Allyl Bromide with Alkyl-selenovinylcoppers from Alkylselenovinyldialkylboranes

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Pages 4369-4373 | Received 01 Apr 1996, Published online: 23 Aug 2006

References

  • Brown , H. C. 1975 . Organic Synthesis via Boranes , New York : Wiley Interscience .
  • Crag , G. M. L. 1973 . Organoboranes in Organic Synthesis , New York : Marcel Dekker .
  • Brown , H. C. and Basawaiah , O. 1983 . J. Org. Chem. , 48 : 5080
  • Tucker , C. E. , Davidson , J. E. and Knochel , P. 1992 . J. Org. Chem. , 57 : 3482
  • Hoshi , M. , Masuda , Y. and Arase , A. 1990 . Bull. Chem. Soc. Jpn. , 63 : 447
  • Hercsi , L. , Heimaus , B. and Allard , C. 1994 . Tetrahedron Lett. , 35 : 6729
  • Raucher , S. , Hansen , M. R. and Colter , M. A. 1978 . J. Org. Chem. , 43 : 4886
  • 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

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