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Studies on sulfinatodehalogenation. XX. Sodium dithionite‐initiated addition of per‐ and polyfluoroalkyl iodides to cyclic enol ethers and chemical conversions of the products
Author(s) -
Huang WeiYuan,
Xie Yuan,
LÜ Long
Publication year - 1991
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.19910090211
Subject(s) - chemistry , sodium dithionite , adduct , acetonitrile , medicinal chemistry , alkyl , aqueous solution , enol , ether , sodium hydride , organic chemistry , catalysis
Per‐ and polyfluoroalkyl iodides [R F I, R F =Cl(CF 2 ) 4 , 1a ; Cl(CF 2 ) 6 , 1b ; Cl(CF 2 ) 8 , 1c ; n ‐C 6 F 13 , 1d ; n ‐C 8 F 17 , 1e ] reacted with cyclic enol ethers such as 2,3‐dihydrofuran (2) and 3,4‐dihydro‐2 H ‐pyran (3) in aqueous acetonitrile in the presence of sodium dithionite and sodium bicarbonate at room temperature (10–15°C) to give the corresponding 2‐( F ‐alkyl) hemiacetals in high yields. The 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 yields. In the presence of p ‐toluenesulfonic acid, the adducts were refluxed in benzene and CH 3 CN to produce the corresponding 2,3‐dihydro‐4‐( F ‐alkyl) furan and 3,4‐dihydro‐5‐( F ‐alkyl)‐2 H ‐pyran. This is a new and effective method for preparing these useful organofluorine compounds.