bis[1-(2-tetrahydrofuranyl)-1,1,3,3,3-pentafluoroisopropyl] terephthalate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis[1-(2-tetrahydrofuranyl)-1,1,3,3,3-pentafluoroisopropyl] terephthalate
• 英文别名: Bis[1,1,1,3,3-pentafluoro-3-(oxolan-2-yl)propan-2-yl] benzene-1,4-dicarboxylate；bis[1,1,1,3,3-pentafluoro-3-(oxolan-2-yl)propan-2-yl] benzene-1,4-dicarboxylate
• 化学式: C₂₂H₂₀F₁₀O₆
• 分子量: 570.381
• InChiKey: JTDPWYDSNADKAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  四氢呋喃 、 bis(α-trifluoromethyl-β,β-difluorovinyl) terephthalate 以100%的产率得到bis[1-(2-tetrahydrofuranyl)-1,1,3,3,3-pentafluoroisopropyl] terephthalate
  参考文献：
  名称：

  Radiation-Induced Radical Polyaddition of Bis(α-trifluoromethyl-β,β-difluorovinyl) Terephthalate with Excess of Various Ethers

  摘要：

  Radiation-induced radical polyaddition of bis(a-trifluoromethyl-P,P-difluorovinyl) terephthalate [CF2=C(CF3)OCOC6H4COOC(CF3)=CF2] (BFP) in the presence of an excess of cyclic and acyclic ethers in feed was examined at 0 degrees C using gamma-ray irradiation. Irradiation of BFP with an 8-fold excess of 1,4-dioxane (DOX) and diethyl ether (EE) gave monomodal polymers consisting of the alternating unit of BFP and DOX moieties (poly(BFP-alt-DOX) (M) over bar (n,as-prepared) 5.1 x 10(3)) and of BFP and EE (poly(BFPalt-EE) (M) over bar (n,as-prepared) = 3.9 x 10(3)), respectively. The irradiation of BFP with an 8-fold excess of tetrahydrofuran or tetrahydropyran provided only 1:2 addition products in high yields. Monofunctional 2-benzoxypentafluoropropene [CF2=C(CF3)OCOC6H5] (BPFP) as a model compound showed preferential formation of the 2:1 adduct to the 1:1 adduct with DOX and EE. The kinetic analysis of the model reactions revealed that the rate constants for the formation of the 2:1 adducts (k(d)) of BPFP with DOX and EE were 2 orders of magnitude higher than those of the 1:1 adducts (k(m)). Poly(BFP-alt-DOX) showed higher radiation resistance than poly(BFP-alt-EE) in solid state as well as in solution. It was concluded that radiation-induced step-growth polymerization under the stoichiometric imbalance of the two compounds requires a high k(d)/k(m) value as well as high radiation resistance for the formation of high molecular weight polymers.

  DOI：

  10.1021/ma051147j

文献信息

• Radiation-Induced Radical Polyaddition of Bis(α-trifluoromethyl-β,β-difluorovinyl) Terephthalate with Excess of Various Ethers
  作者：Kazuyuki Enomoto、Yasunari Maekawa、Yosuke Katsumura、Toyoaki Miyazaki、Masaru Yoshida、Hiroshi Hamana、Tadashi Narita

  DOI：10.1021/ma051147j

  日期：2005.11.1

  Radiation-induced radical polyaddition of bis(a-trifluoromethyl-P,P-difluorovinyl) terephthalate [CF2=C(CF3)OCOC6H4COOC(CF3)=CF2] (BFP) in the presence of an excess of cyclic and acyclic ethers in feed was examined at 0 degrees C using gamma-ray irradiation. Irradiation of BFP with an 8-fold excess of 1,4-dioxane (DOX) and diethyl ether (EE) gave monomodal polymers consisting of the alternating unit of BFP and DOX moieties (poly(BFP-alt-DOX) (M) over bar (n,as-prepared) 5.1 x 10(3)) and of BFP and EE (poly(BFPalt-EE) (M) over bar (n,as-prepared) = 3.9 x 10(3)), respectively. The irradiation of BFP with an 8-fold excess of tetrahydrofuran or tetrahydropyran provided only 1:2 addition products in high yields. Monofunctional 2-benzoxypentafluoropropene [CF2=C(CF3)OCOC6H5] (BPFP) as a model compound showed preferential formation of the 2:1 adduct to the 1:1 adduct with DOX and EE. The kinetic analysis of the model reactions revealed that the rate constants for the formation of the 2:1 adducts (k(d)) of BPFP with DOX and EE were 2 orders of magnitude higher than those of the 1:1 adducts (k(m)). Poly(BFP-alt-DOX) showed higher radiation resistance than poly(BFP-alt-EE) in solid state as well as in solution. It was concluded that radiation-induced step-growth polymerization under the stoichiometric imbalance of the two compounds requires a high k(d)/k(m) value as well as high radiation resistance for the formation of high molecular weight polymers.