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ω-氯氟烷基醇,烯烃及环氧化物的合成

Synthesis of ω-Chloroperfluoroalkylated Alcohols, Olefines and Epoxides

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【作者】 郭彩云王珊娣

【Author】 GUO Cai-Yun, WANG San-Di(Shanghai Institute of organic Chemistry, Chinese Academy of Sciences, 200032 Shanghai)

【机构】 中国科学院上海有机化学研究所中国科学院上海有机化学研究所 上海200032上海200032

【摘要】 <正> 全氟烷基碘的加成反应一直活跃在氟化学中,即使近来也依然受到注意,这是因为由它们出发可做许多有用的中间体,其中氟烷基取代的醇可做织物表面处理剂,氟烷基取代的环氧化合物可做润滑剂。我们曾用引发剂,使ψ—碘代全氟烷基磺酰氟与多键类化合物在较温和条件下进行加成。黄维垣教授等用NaHCO3—K3[Fe(CN)6]引发Cl(CF24.6I与烯丙醇顺利加成。

【Abstract】 The free radical addition of Cl(CF2)nI (n = 2,4,6,8) la to allylic compounds (CH2 = CH -CH2X, X = OH, OAc) and vinyl acetate in the presence of initiator gave the corresponding adducts Cl(CF2)nCH2CHICH2OH (2a- d), Cl(CF2)nCH2CHICH2OAc (3a- d) and Cl(CF2)n-CH2CHIOAc (4a- d) with good yields. The deiodination of 2a- d to Cl(CF2)nCH2CH2CH2OH (5a- d) by LiAlH4 went smoothly. The alcohol Cl(CF2)nCH = CHCH2OH 6a- c was formed fromthe reaction of 2a- d with KOH-methanol, however, the opoxide Cl(CF2)nCH2-CH-CH2(7a- d) was obtained with aqueous NaOH. Zinc reduction of 2a- d and 3a- d in isopropanol in the presence of small amounts of acetic acid afforded the elimination products Cl (CF2)n-CH2CH = CH2(8a- d). Contrarily the reduction of 4a- d with Zinc, followed by hydrolysis with KOH-methanol-water gave clearly C1(CF2)n (CH2)2OH (10a- d).

【关键词】 氟烷基碘环氧化合物
【Key words】 iodofluoroalkanealcoholepoxide
  • 【文献出处】 有机化学 ,Chinese Journal of Organic Chemistry , 编辑部邮箱 ,1994年02期
  • 【分类号】O623
  • 【被引频次】1
  • 【下载频次】94
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