有机化学 ›› 2003, Vol. 23 ›› Issue (2): 120-128. 上一篇    下一篇

研究论文

Ramberg-Backlund反应在构筑碳碳双键中的应用

王小龙;曹小平;周兆丽   

  1. 兰州大学化学化工学院,兰州(730000)
  • 发布日期:2003-02-25

Application of Ramberg-Backlund reaction in construction of carbon- carbon double bond

Wang Xiaolong;Cao Xiaoping;Zhou Zhaoli   

  1. National Laboratory of Applied Organic Chemistry,College of Chemistry and Chemical Engineering ,Lanzhou University,Lanzhou(730000)
  • Published:2003-02-25

碳碳双键是有机化学中最基本的官能团之一,在众多的构筑碳碳双键的方法中 Ramberg-Baecklund反应占有很重要的地位。该方法的关键步骤是α-卤代砜在碱 性条件下,发生1,3-消除反应,得到环状砜,然后重排失去SO2形成双键,这样 形成的双键位置确定,即具有良好的区域选择性,并且在不同的反应条件下可得到 不同构型的产物,因而在有机合成中有很好的应用前景,对Ramberg-Baecklund反 应进行了较为详细的综述,并对我国实验室所进行的反应条件的改进和优化以及目 前的研究进展作了总结。

关键词: 共轭双键化合物, 选择性, 碳-碳键

The carbon-carbon double bond is one of the most fundamental functional groups in organic chemistry. In the ever-expanding modern organic synthesis methods, the Ramberg-Backlund reaction continues to occupy a prominent position among various methods for the construction of carbon-carbon double bond. On treament with base, a-halo sulfones were converted into alkenes via Ramberg-Backlund reaction. It is now understood that the reaction takes place via 1, 3-elimination of HX from the a-halo sulfones, and loss of SO-2 from the resulting thiirane 1,1-dioxide. Because Ramberg-Backlund reaction has good stereoselective, it provides convenient and versatile route to polysubstituted alkenes. In this review, we focus on the modification and application of Ramberg-Backlund reaction. The research works in our laboratory are also discussed.

Key words: CONJUGATED DOUBLE BOND COMPOUNDS, SELECTIVITY, CARBON-CARBON BOND

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