4,4'-bis(3-chlorophenoxy)biphenyl | 153288-03-0

• 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: 4,4'-bis(3-chlorophenoxy)biphenyl
• 英文别名: 1-Chloro-3-[4-[4-(3-chlorophenoxy)phenyl]phenoxy]benzene
• CAS: 153288-03-0
• 化学式: C₂₄H₁₆Cl₂O₂
• 分子量: 407.296
• InChiKey: QOFBEJYNNMEYJT-UHFFFAOYSA-N

物化性质

• 沸点：
  517.9±50.0 °C(predicted)
• 密度：
  1.273±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4,4'-bis((η6-3-chlorophenoxy-η5-cyclopentadienyl)iron)biphenyl hexafluorophosphate 以 二氯甲烷 、 乙腈 为溶剂， 以94%的产率得到4,4'-bis(3-chlorophenoxy)biphenyl
  参考文献：
  名称：

  双（环戊二烯基铁）芳烃配合物：合成和官能化聚芳醚的新途径

  摘要：

  A new development in the chemistry of arenes activated toward S(N)Ar reactions by the cyclopentadienyliron (FeCp+) moiety is presented in this work. A class of diiron complexes of diphenoxybenzenes was prepared in a highly efficient and very mild fashion. Dihydroxyaromatic compounds served as dinucleophiles, allowing for the formation of the diiron complexes. This could be achieved in either a one or two step procedure. A wide variety of dinucleophiles were incorporated into this study, as well as a number of FeCp+ activated arenes. It is shown that these reactions are not inhibited by bulky substituents on either the dinucleophiles or activated arenes. The diiron complexes themselves could also undergo S(N)Ar reactions, provided that the complexed arenes contained a chlorine substituent. This allowed for the functionalization of the complexes with species that could not be introduced directly in their syntheses. The carbon nucleophiles generated from ethyl cyanoacetate or (phenylsulfonyl)acetonitrile could be attached to the complexed ethers in this manner. The FeCp+ moieties were removed easily by photolytic demetalation which allowed for the recovery of a wide range of functionalized diphenoxybenzenes. This methodology is advantageous over all those previously reported and should be a practical route to the synthesis of aromatic ethers.

  DOI：

  10.1021/om00013a055

文献信息

• Bis(cyclopentadienyliron)arene complexes: a new route to the synthesis and functionalization of polyaromatic ethers
  作者：Alaa S. Abd-El-Aziz、David C. Schriemer、Christine R. de Denus

  DOI：10.1021/om00013a055

  日期：1994.1

  A new development in the chemistry of arenes activated toward S(N)Ar reactions by the cyclopentadienyliron (FeCp+) moiety is presented in this work. A class of diiron complexes of diphenoxybenzenes was prepared in a highly efficient and very mild fashion. Dihydroxyaromatic compounds served as dinucleophiles, allowing for the formation of the diiron complexes. This could be achieved in either a one or two step procedure. A wide variety of dinucleophiles were incorporated into this study, as well as a number of FeCp+ activated arenes. It is shown that these reactions are not inhibited by bulky substituents on either the dinucleophiles or activated arenes. The diiron complexes themselves could also undergo S(N)Ar reactions, provided that the complexed arenes contained a chlorine substituent. This allowed for the functionalization of the complexes with species that could not be introduced directly in their syntheses. The carbon nucleophiles generated from ethyl cyanoacetate or (phenylsulfonyl)acetonitrile could be attached to the complexed ethers in this manner. The FeCp+ moieties were removed easily by photolytic demetalation which allowed for the recovery of a wide range of functionalized diphenoxybenzenes. This methodology is advantageous over all those previously reported and should be a practical route to the synthesis of aromatic ethers.