Acta Chimica Sinica ›› 1983, Vol. 41 ›› Issue (10): 946-959. Previous Articles     Next Articles

Original Articles

全氟和多氟烷基磺酸的研究 IX. 5-卤-3-氧杂-全氟戊磺酰氟的化学转化

苏德宝;陈庆云;朱蓉仙;胡海平   

  1. 中国科学院上海有机化学研究所
  • 发布日期:1983-10-15

Perfluoro and polyfluorosulfonic acids IX: Some chemical transformations of 5-halo-3-oxa- perfluoropentanesulfonyl fluoride

SU DEBAO;CHEN QINGYUN;ZHU RONGXIAN;HU HAIPING   

  • Published:1983-10-15

5-Halo-3-oxa-perfluoropentanesulfonic acids 2,4 were obtained in high yields by treating the corresponding sulfonyl fluorides successively with KOH and concentrated H2SO4: Treatment of the acids with P2O5 gave corresponding anhydrides 3, 5. 3 reacted with various alcohols in the presence of pyridine to yield sulfonates 6. 5-Iodo-3-oxa-perfluoropentanesulfonyl fluoride (1) was converted to the acyl fluoride 9 by fuming sulfuric acid. Depending on the reaction temperature 9 can be hydrolyzed to fluorosulfonyl perfluoroalkanoic acid 10 and/or mixed dibasic acid 11. A similar phenomenon was also observed in the case of hydrolysis of fluorocarbonyl-perfluoromethanesulfonyl fluoride(13). Alcohol reacted readily with the acyl fluoride group but not with the sulfonyl group in 9 giving carboxylic esters, which can be further transformed to the corresponding sulfonates. Perfluoroalkoxide ion -O(CF2)2O(CF2)2SO2F prepared from 9 and F- reacted with active alkyl halides yielding the corresponding ethers. The interaction of 5-halo-3-oxa-perfluoroalkane-sulfonyl fluoride with AlCl3 was investigated. Friedel-crafts acylation of aromatic compounds with 9 in the presence of anhydrous AlCl3 is also reported. The yields of the desired ketones can be improved by using CCl4 as a solvent and changing the order of addition of reactants.

Key words: ALKANE, SULFONIC ACID, ACYL FLUORIDES, CHEMICAL CHANGE, FLUOROCARBON

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