4,4,5,5,6,6,6-Heptafluoro-2-iodohexanenitrile

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4,4,5,5,6,6,6-Heptafluoro-2-iodohexanenitrile
• 化学式: C₆H₃F₇IN
• 分子量: 348.99
• InChiKey: DXGHWJIISSCKQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  七氟-1-碘丙烷 、 丙烯腈 反应 36.0h， 以32%的产率得到2-Iodo-4-(2,2,3,3,4,4,4-heptafluorobutyl)pentanedinitrile
  参考文献：
  名称：

  Reaction of Perfluoroalkyl Iodides with Electron-Deficient Olefins under UV Irradiation

  摘要：

  The reaction of perfluoroalkyl iodides 1 with acrylates, acrylic acid, acrylamide, and acrylonitrile has been investigated. In the presence of a catalytic amount of palladium(0), the reaction of R(f)I with ethyl acrylate produces: mostly polymer. Under irradiation with 254 nm UV light, perfluoroalkyl iodides react with. ethyl acrylate to give high yields of the 1:1 addition products (74-88% isolated yield, CnF(2n+1)CH(2)CHICO(2)Et) and small amounts of 1:2 adducts (<10% NMR yield) at ambient temperature. The functionalized iodide 5-iodo-3-oxaoctafluoropentanesulfonyl fluoride also reacts with ethyl acrylate to give the 1:1 adduct in 88% yield. However, it has been found that the reaction selectivity is related to the length of the perfluoroalkyl group in 1 when methyl acrylate is employed in the reaction under similar conditions. Both 1:1 (56-76%) and 1:2 adducts [CnF(2n+1)- CH2CH(CO(2)Me)CH(2)CHICO(2)Me, 24-34%] are formed when methyl acrylate reacts with short-chain perfluoroalkyl iodides [CnF(2n+1)I, n less than or equal to 4], whereas the reaction of perfluorohexyl or longer chain perfluoroalkyl iodides [CnF(2n+1)I, n greater than or equal to 6] gives predominantly the 1:1 addition products (>85%). The formation of the 1:2 adduct can be efficiently suppressed by using excess R(f)I in the reaction. The reaction of N,N-dimethylacrylamide with perfluoropropyl iodide (1a) produces exclusively the 1:1 adduct. Products from the further elimination, reduction, and decarboxylation of the 1:1 and 1:2 adducts are observed when 1a reacts with methyl methacrylate under similar conditions. The reaction of 1a with acrylonitrile produces the 1:1 and 1:2 adducts in 53% and 47% yields, respectively. An addition-reduction product, n-C3F7CH2CH2CO2H (68%), is obtained in the reaction of acrylic acid with 1a.

  DOI：

  10.1021/jo00116a038

文献信息

• Reaction of Perfluoroalkyl Iodides with Electron-Deficient Olefins under UV Irradiation
  作者：Zai-Ming Qiu、Donald J. Burton

  DOI：10.1021/jo00116a038

  日期：1995.6

  The reaction of perfluoroalkyl iodides 1 with acrylates, acrylic acid, acrylamide, and acrylonitrile has been investigated. In the presence of a catalytic amount of palladium(0), the reaction of R(f)I with ethyl acrylate produces: mostly polymer. Under irradiation with 254 nm UV light, perfluoroalkyl iodides react with. ethyl acrylate to give high yields of the 1:1 addition products (74-88% isolated yield, CnF(2n+1)CH(2)CHICO(2)Et) and small amounts of 1:2 adducts (<10% NMR yield) at ambient temperature. The functionalized iodide 5-iodo-3-oxaoctafluoropentanesulfonyl fluoride also reacts with ethyl acrylate to give the 1:1 adduct in 88% yield. However, it has been found that the reaction selectivity is related to the length of the perfluoroalkyl group in 1 when methyl acrylate is employed in the reaction under similar conditions. Both 1:1 (56-76%) and 1:2 adducts [CnF(2n+1)- CH2CH(CO(2)Me)CH(2)CHICO(2)Me, 24-34%] are formed when methyl acrylate reacts with short-chain perfluoroalkyl iodides [CnF(2n+1)I, n less than or equal to 4], whereas the reaction of perfluorohexyl or longer chain perfluoroalkyl iodides [CnF(2n+1)I, n greater than or equal to 6] gives predominantly the 1:1 addition products (>85%). The formation of the 1:2 adduct can be efficiently suppressed by using excess R(f)I in the reaction. The reaction of N,N-dimethylacrylamide with perfluoropropyl iodide (1a) produces exclusively the 1:1 adduct. Products from the further elimination, reduction, and decarboxylation of the 1:1 and 1:2 adducts are observed when 1a reacts with methyl methacrylate under similar conditions. The reaction of 1a with acrylonitrile produces the 1:1 and 1:2 adducts in 53% and 47% yields, respectively. An addition-reduction product, n-C3F7CH2CH2CO2H (68%), is obtained in the reaction of acrylic acid with 1a.