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新型高效合成α-碘代-α,α-二氟和β-碘代-α,α,β,β-四氟羧酸衍生物,作为制备功能性含氟化合物的有用构建单元。

New and efficient syntheses of alpha-iodo-alpha,alpha-difluoro- and beta-iodo-alpha,alpha,beta,beta-tetrafluorocarboxylic acid derivatives as useful building blocks for making functional fluoro compounds.

作者信息

Hung Ming-H, Long Lu, Yang Zhen-Yu

机构信息

DuPont Dow Elastomers, L.L.C., and DuPont Central Research and Development, Experimental Station, Wilmington, Delaware 19880, USA.

出版信息

J Org Chem. 2004 Jan 9;69(1):198-201. doi: 10.1021/jo035170j.

DOI:10.1021/jo035170j
PMID:14703399
Abstract

Perfluoroolefins reacted with I-Cl and ClSO(3)H under mild conditions to give R(F)CFICF(2)OSO(2)Cl, which could be readily converted into various alpha-iodo-perfluorocarboxylic acid derivatives or telomerized with tetrafluoroethylene to I(CF(2)CF(2))(n)()OSO(2)Cl. Ring-opening reaction of perfluoroalkoxypentafluorocyclopropane with iodine at 240 degrees C produced ICF(2)CF(2)COF, which was quenched by alcohol, water, or NH(3) to give beta-iodo-alpha,alpha,beta,beta-tetrafluorocarboxylic acid derivatives. These functional fluorinated iodides can be used as building blocks for making selectively fluorinated compounds.

摘要

全氟烯烃在温和条件下与一氯化碘和氯磺酸反应,生成R(F)CFICF(2)OSO(2)Cl,它可很容易地转化为各种α-碘全氟羧酸衍生物,或与四氟乙烯发生调聚反应生成I(CF(2)CF(2))(n)()OSO(2)Cl。全氟烷氧基五氟环丙烷在240℃下与碘发生开环反应生成ICF(2)CF(2)COF,它可被醇、水或氨淬灭,得到β-碘-α,α,β,β-四氟羧酸衍生物。这些功能性氟化碘化物可用作制备选择性氟化化合物的基础原料。

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