((diphenylmethyl)oxy)ferrocene | 1246225-66-0

• 英文名称: ((diphenylmethyl)oxy)ferrocene
• CAS: 1246225-66-0
• 化学式: C₂₃H₂₀FeO
• 分子量: 368.258
• InChiKey: QLTOPAJKHNGEER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为产物：
  描述：

  iodoferrocene 、 benzhydrol sodium salt 在 CuI 、 2,2'-bipyridine 作用下， 以 further solvent(s) 为溶剂， 以76%的产率得到((diphenylmethyl)oxy)ferrocene
  参考文献：
  名称：

  铜（I）介导的二茂铁烷基醚的合成†

  摘要：

  碘化二茂铁与各种醇盐的铜（I）介导的Ullman型偶联已用于制备一系列二茂铁基烷基醚。以这种方式，可以以良好的产率获得不能通过经典的威廉姆森醚合成法合成的氧取代的二茂铁。报告了三个固态样品的结构。

  DOI：

  10.1021/om1006209

文献信息

• Nucleophilic Aromatic Substitution Reactions for the Synthesis of Ferrocenyl Aryl Ethers
  作者：Marcus Korb、Pieter J. Swarts、Dominique Miesel、Alexander Hildebrandt、Jannie C. Swarts、Heinrich Lang

  DOI：10.1021/acs.organomet.6b00157

  日期：2016.5.9

  A range of ferrocenyl aryl ethers of type Fc-O-Ar (Fc = Fe(eta(5)-C6H5)(eta(5)-C6H(n)X(4-n)); n = 2-4; X = H, P(O)(OEt)(2) SO2CF3; Ar = 2,4-(NO2)(2)-C6H3, 4-NO2-C6H4) have been successfully prepared by using the nucleophilic aromatic substitution reaction (SNAr) of Fc-OLi (1a-Li) and electron-deficient aryl fluorides, enabling a new pathway to this rarely described family of organometallic compounds. Initial studies of 1a-Li and o-phosphonato-substituted hydroxyferrocenes (1b-Li) have also been performed, indicating a low nudeophilicity of the oxygen atom. The SNAr reaction protocol tolerates ortho substituents, e.g. phosphonato and sulfonyl groups, resulting in 1,2-X,O (X = S, P) ferrocenyl ethers that can be obtained in a one pot synthesis procedure including 1,3-O -> C anionic phospho- and thia-Fries rearrangements. Within these studies, the first 1,3-diortho-functionalized ferrocenyl aryl ether could be synthesized. An electrochemical study of the redox potentials of the obtained compounds allows conclusions on the reactivity of the varying electronic properties and the electrophilicity of different aryl fluorides and the nucleophilicity of the functionalized hydroxyl ferrocenes, which is directly reflected by the potential of the first ferrocene related redox processes. Chiral-pool-based phosphonates rearrange to the aryl ethers with diastereomeric excesses of 74 and 81% after the anionic Fries rearrangement. The usage of aryl 1,2-/1,3-difluorides resulted in the synthesis of the first examples of bis(FcO)-substituted benzenes. Their electrochemical investigations reveal a splitting of the two redox processes of the ferrocenyls that decreases from 155 mV (1,2-substitution) to 130 mV (1,3-substitution) on the basis of electrostatic interactions.