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化学学报
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化学学报 ›› 2001, Vol. 59 ›› Issue (9): 1507-1512. 上一篇    下一篇

研究论文

β-Oxido膦叶立德的亲卤反应: 一种便利地合成三取代卤代烯 烃的方法

张雄志;胡金山;李兴亚;傅伟敏   

  1. 中国科学院上海有机化学研究所.上海(200032)
  • 发布日期:2001-09-15

Novel reactions of β-Oxidophosphonium ylides with perhaloalkanes: A facile route to trisubstituted halo olefins

Zhang Xiongzhi;Hu Jinshan;Li Xingya;Fu Weimin   

  1. Shanghai Inst Organ Chem., CAS.Shanghai(200032)
  • Published:2001-09-15

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β-Oxido膦叶德作为新核试剂对一系列全卤代烷烃中的碳卤键能顺利地进行新卤进攻，生成α-卤代betaine中间体，并由此直接转化成相应的以Z式构型为主、反应产率中等的氯代、溴代或碘代的三取代烯烃。利用不同结构的鏻盐和醛缩合而? 傻摩?Oxido膦叶立德与全卤代烷反应，可以方便地合成一系列不同的结构的三取? 贝┨? $601$Aβ-OxidophosphoniumylidesasnucleophilesreactreadilywithvariousperhalalkanesviahalophilicattackonC—X(X=I,BrorCl)bondstoformaα-halosubstitutedbetaineintermediates,whichcanbetransformedinsituintoZ-isomersofchloro-,bromo-oriodo-substitutedolefinsasmajorproductsingoodyields.Thesenovelreactiosnmayaffordafacileroutetovarioustrisubsitutedhaloolefinsbymeansofβ-Oxidophosphoniumylidespreparedinsitufromvariousphosphoniumsaltsandaldehydes.

关键词: 膦叶立德, 亲卤反应, 卤代烃, 烯烃

β-Oxidophosphonium ylides as nucleophiles react readily with various perhalalkanes via halophilic attack on C—X(X=I,Br or Cl) bonds to forma α-halosubstituted betaine intermediates, which can be transformed in situ into Z-isomers of chloro-, bromo- or iodo- substituted olefins as major products in good yields. These novel reactiosn may afford a facile route to various trisubsituted halo olefins by means of β-Oxidophosphonium ylides prepared in situ from various phosphonium salts and aldehydes.

Key words: HALOHYDROCARBON, ALKENE

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