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化学学报
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化学学报 ›› 1982, Vol. 40 ›› Issue (4): 337-352. 上一篇    下一篇

论文

全氟和多氟烷基磺酸的研究Ⅳ.3-氧杂多氟烷烃磺酸酯的合成及其硫-氧和碳-氧键的断裂

陈庆云, 朱蓉仙, 李宗珍, 王珊娣, 黄维垣   

  1. 中国科学院上海有机化学研究所
  • 投稿日期:1980-12-15 发布日期:2013-06-03
  • 通讯作者: 陈庆云

PERFLUORO AND POLYFLUOROSULFONIC ACIDS Ⅳ. THE SYNTHESIS OF 3-OXAPOLYFLUOROALKANESULFONATES AND THEIR SULFUR-OXYGEN VERSUS CARBON-OXYGEN SCISSION

CHEN QING-YUN, ZHU RONG-XIAN, LI ZONG-ZHEN, WANG SHAN-DI, HUANG WEI-YUAN   

  1. Shanghai Institute of Organic Chemistry, Academia Sinica
  • Received:1980-12-15 Published:2013-06-03

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被引次数

10

以3-氧杂多氟烷烃磺酰氟XOCF2CF2SO2F为原料,在二氯甲烷中于-20～-30℃与三乙胺、含氟醇或苯酚反应得到一系列氧杂多氟磺酸酯XOCF2CF2SO3R(1a～1g),产率52～90%.影响产率的主要因素是反应温度,而不是碱用量.亲核试剂与这些磺酸酯作用,主要引起酯基的C—O断裂.如1a或1c与I,CNS和R1R2NH反应得HCF2CF2CH2Y(Y=I,CNS,R1R2N),与HCF2CF2CH2θ得对称醚(HCF2CF2CH2)2O.

α,α,ω-Tri-H-perfluoroalkyl and phenyl 3-oxapolyfluoroalkanesulfonates XOCFaCFaO3R [R=HCFaCFaCHa,X=ICF2CF2 (1 a),CH3(1b),Cl2CFCF2 (1c),HOF2CF2CH2 (1d);R=H(CF2CF2)2CH2: X=Cl2CFCF2(1e);R=O6H5:X=CF2CF2 (1f); Cl2CFCF2 (1g)].were synthesized by the reactions of 3-ogaperfluoroalkanesulfonyl fluorides with 1,1,3-tri-H-tetraflnoropropanol,1,1,5-tri-H-perfluoropentanol and phenol respectively in 50-90% yields.The main factor affecting the yield,of the sulfonates was the reaction temperature,not the amount of base used.The sulfuroxygen and/or carbon-oxygen scissions can occur in these snlfona,tes during nucleophilic substitution.