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化学学报
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化学学报 ›› 1989, Vol. 47 ›› Issue (2): 141-146. 上一篇    下一篇

研究论文

亚磺化脱卤研究 X: 全氟及多氟溴代烷的反应研究

黄维垣;王巍   

  1. 中国科学院上海有机化学研究所
  • 发布日期:1989-02-15

Studies on sulfinatodehalogenation X: The reaction of perfluoro- and polyfluoroalkyl bromides

HUANG WEIYUAN;WANG WEI   

  • Published:1989-02-15

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本文报道溴代全氟烷和α,ω-二溴代全氟烷在亚磺化脱卤反应体系中与烯烃的反应及其与相应的碘代全氟烷的区别. 合成了全氟仲溴代烷CF3CFBrOCF2CF(CF3)O(CF2)2SO2F(7), 它与烯烃反应可得到1:1的加成物. 7的水解产物CF3CFBrOCF2CF(CF3)O(CF2)2SO3Na(11)与连二亚硫酸钠反应只得到氢化脱溴产物. 多氟溴化物CF3CBr2X(13X=F; 14X=Cl; 15X=Br)经亚磺化脱溴可得到相应的亚磺酸钠盐CF3CBrXSO2Na(16X=F; 17X=Cl; 18X=Br), 其中间体多氟烷自由基可用烯烃捕集, 得到高产率的1:1加成产物.

关键词: 烯烃, 溴代烃, 烷烃 P, 自由基反应, 脱卤反应, 全氟代烃, 亚磺化

The reaction of perfluoroalkyl bromide and a,w-perfluoralkylene dibromide in sulfinatodehalogenation system with olefins and the differences in behavior between perfluoroalkyl bromides and their corresponding iodides are reported. The secondary perfluoroalkyl bromide CF3CFBrOCF2CF(CF3)O(CF2)2SO2F was synthesized and reacted with olefins to give 1:1 adducts. However, the sulfonate CF3CFBrOCF2CF(CF3)O(CF2)2SO3Na reacted with sodium dithionite to give only the hydrodebromination product. The polyfluoroalkyl bromides CF3CBr2R (R = F, Cl, Br) reacted normally to give the corresponding sodium sulfinate CF3CBrRSO2Na. The reaction intermediate polyfluoroalkyl radical can also be trapped by olefins to give good yields of 1:1 adducts.

Key words: ALKENE, BROMOHYDROCARBON, ALKANE P, FREE RADICAL REACTION, DEHALOGENATION REACTION, PERFLUORO-HYDROCARBON, SULFINATION

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