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学科主题: 有机氟化学
题名: The activation of carbon-chlorine bonds in per-and polyfluoroalkyl chlorides: DMSO-induced hydroperfluorolkylation of alkenes and alkynes with sodium dithionite
其他题名: 全氟和多氟烷基氯中碳-氯键的行为:DMSO 引导下连二亚硫酸钠作用下烯(炔)烃的氢代全氟烷基化
作者: Long ZY(龙正宇) ; Chen QY(陈庆云)
通讯作者: 陈庆云
刊名: J. Org. Chem.
发表日期: 1999-01-01
卷: 64, 期:13, 页:4775-4782
收录类别: SCI
部门归属: 中国科学院上海有机化学研究所有机氟化学开放实验室
英文摘要: In DMSO, the addition reacions of perfluoroalkyl chlorides, R=fCl, to alkenes or alkynes can occur smoothly in the presence of 1.5 equiv of Na=2S=2O=4 and NaHCO=3 at 75-80℃ for 4-10 h to give the corresponding adducts (RCH=2CH=2R=F or RCH=CHR=F). Ethyl chlorofluoro-(1f), chlorodifluoro-(1g) acetates, even nonfluorinatedcompounds, such as ethyl dichloro-(1h), chloro-(1i) acetates, and chloroform (1j) can undergo the similar reaction. Treatment of ω-iodo (or chloro-)perfluoroalkyl chlorides [X(CF=2)=nCl,n=2,4X=I or Cl] with >3 equiv of alkenes and Na=2S=2O=4 gives directly the symmetrically disubstituted alkanes (RCH=2CH=2)=2(CF=2)=n. The symmetrically and unsymmetrically disubstituted adducts RCH=2CH=2(CF=2)=n CH=2CH=2R' from ω-iodoperfluoroalkyl chlorides can be also obtained stepwise, I.e., through the further addition reactions of monoadducts, RCH=2CH=2(CF=2)n Cl to olefins. However, for αω-dichloroperfluoroalkyanes, the similarly stepwise reactions with an alkene is not clean, both bis-adducts and the corresponding ω-hydrides, RCH=2CH=2(CF=2)n H as byproducts are also formed. In the absence of alkenes or alkynes, per-and polyfluoroalkyl chlorides can be converted to their sulfinate salts and sulfonyl chlorides.
语种: 英语
相关网址: 查看原文
内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/13514
Appears in Collections:中科院有机氟化学重点实验室_期刊论文

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Recommended Citation:
Long ZY,Chen QY. The activation of carbon-chlorine bonds in per-and polyfluoroalkyl chlorides: DMSO-induced hydroperfluorolkylation of alkenes and alkynes with sodium dithionite[J]. J. Org. Chem.,1999,64(13):4775-4782.
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