有机化学 ›› 2006, Vol. 26 ›› Issue (02): 158-167. 上一篇    下一篇

综述与进展

Ramberg-Bäcklund反应在功能有机分子合成中的应用

冯建鹏,王小龙,曹小平*   

  1. (兰州大学化学化工学院 功能有机分子化学国家重点实验室 兰州 730000)
  • 收稿日期:2005-02-21 修回日期:2005-06-16 发布日期:2006-01-21
  • 通讯作者: 曹小平

Application of Ramberg-Bäcklund Reaction to the Synthesis ofFunctional Organic Molecule

FENG Jian­Peng,WANG Xiao­Long,CAO Xiao­Ping*   

  1. (State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineer-ing,
    Lanzhou University, Lanzhou 730000)
  • Received:2005-02-21 Revised:2005-06-16 Published:2006-01-21
  • Contact: CAO Xiao­Ping

碳碳双键广泛地存在于功能有机分子中, 其构筑在合成化学中具有极其重要的意义. Ramberg-Bäcklund反应是构筑碳碳双键的重要方法之一, 其关键步骤是砜在碱性条件下进行1,3-消除, 得到环状砜, 然后重排除去SO2形成双键.该方法具有良好的立体选择性, 底物在不同的反应条件下得到不同构型的产物, 因而可以应用于合成许多功能有机分子, 具有很好的应用前景. 结合自己的研究工作对Ramberg-Bäcklund反应在功能有机分子合成中的应用进行了较为系统的总结, 也对Ramberg-Bäcklund反应的拓展进行了简要介绍.

关键词: Ramberg-Bä, 应用, cklund反应, 构筑碳碳双键, 功能有机分子

It is important to construct carbon-carbon double bond skeleton in the organic synthesis using Ramberg-Bäcklund reaction. On the treatment with base, the α-halo sulfone was converted into alkene. It is now understood that the reaction takes place via 1,3-elimination of halide from the sulfone α-anion, and loss of SO2 from the resulting 1,1-dioxothiirane. Ramberg-Bäcklund reaction has good stereoselectivity to the construction of the carbon-carbon double bond. Here a brief historical review of Ramberg-Bäcklund reaction was presented along with a detail summary of its application to the synthesis of functional organic molecules, including recent developments in this area originating from the author’s laboratory.

Key words: cklund reaction, application, construction of carbon-carbon double bond, functional organic molecule, Ramberg-Bä