Studies on sulfinatodehalogenation——ⅩⅩ.Sodium dithionite-initiated addition of per-and polyfluoroalkyl iodides to cyclic enol ethers and chemical conversions of the products

作     者：HUANG Wei-Yuan XIE Yuan-Lv Long Shanghai 

作者机构：Institute of Organic ChemistryThe Chinese Academy of SciencesShanghai 200032 

出 版 物：《Chinese Journal of Chemistry》 (中国化学（英文版）)

年 卷 期：1991年第9卷第2期

页      面：167-173页

核心收录：

学科分类：07[理学] 0703[理学-化学] 

基　　金：This work is financially supported by the National Natural Science Foundation of China 

主　　题：Studies on sulfinatodehalogenation CF Sodium dithionite-initiated addition of per-and polyfluoroalkyl iodides to cyclic enol ethers and chemical conversions of the products 

摘      要：Per-and polyfluoroalkyl iodides[R_FI,R_F=Cl(CF_2)_4,1a;Cl(CF_2)_6,1b;Cl(CF_2)_8,1c;n- C_6F_(13),1d;n-C_8F_(17),1e]reacted with cyclic enol ethers such as 2,3-dihydrofuran(2)and 3,4-dihydro- 2H-pyran(3)in aqueous acetonitrile in the presence of sodium dithionite and sodium bicarbonate at room temperature(10—15℃)to give the corresponding 2-(F-alkyl)hemiacetals in high *** adducts were oxidized with Ce(NH_4)_2(NO_3)_6 in acetonitrile or reduced with LiAlH_4 in ether to form the corresponding 2-(F-alkyl)lactones or diols respectively in good *** the presence of p- toluenesulfonic acid,the adducts were refluxed in benzene and CH_3CN to produce the corresponding 2,3-dihydro-4-(F-alkyl)furan and 3,4-dihydro-5-(F-alkyl)-*** is a new and effective method for preparing these useful organofluorine compounds.