Chin. J. Org. Chem. ›› 2008, Vol. 28 ›› Issue (08): 1487-1489. Previous Articles     Next Articles



夏 湘a,b ; 邹康兵a; 方大为a; 许新华*,b   

  1. (a湖南邵阳学院生物与化学工程系 邵阳 422400)
    (b湖南大学化学化工学院 长沙 410082)
  • 收稿日期:2007-09-04 修回日期:2008-05-10 发布日期:2008-08-18
  • 通讯作者: 许新华

Cesium Hydroxide Promoted Reaction of Element Selenium with Terminal Alkynes and Alkyl Halides to Synthesize Acetylenic Selenides

XIA, Xiang a,b; ZOU, Kang-Binga ; FANG, Da-Wei a; XU, Xin-Hua*,b   

  1. (a Department of Biological and Chemical Engineering, Shaoyang University, Shaoyang 422400, China)
    (b College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China)

  • Received:2007-09-04 Revised:2008-05-10 Published:2008-08-18
  • Contact: XU, Xin-Hua

In the presence of 4Å MS, a mixture of terminal acetylene, cesium hydroxide and element selenium in DMF was stirred under N2 atomsphere at room temperature for 2 h, then alkyl bromides or diaryliodonium salts were added to the mixture and the resulting mixture was stirred at room temperature for 20 h to give acetylenic selenides in about 60% yields. The mechanism involved the reaction of terminal acetylene with cesium hydroxide to form the cesium alkynide, then selenium inserted into C—Cs bond and gave the cesium alkynylselenoate, which underwent nucleophilic substitution with alkyl bromides or diaryliodonium salts to give the corresponding acetylenic selenides.

Key words: cesium hydroxyl, diaryliodonium salt, alkyl halide, selenium, acetylenic selenide