Generation and Properties of a Cyclopentadienyl Cation Annelated with Homoadamantene Frameworks

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Other Title
  • ホモアダマンテンが縮環したシクロペンタジエニルカチオンの発生と性質

Description

Reports on experimental studies on Cp cations are quite limited due to their intrinsic instability because of the antiaromaticity. Annelation of rigid cycloalkene framework(s) would be an effective way to stabilize such labile pi-conjugated cationic species. We report here the generation and reaction of a new phenyl-substituted Cp cation, annelated with two homoadamantene frameworks. The Cp cation was generated using a newly synthesized chloride as a precursor either by i) methanolysis or ii) abstraction of chloride ion by Ag+ or B(C6F5)3 in dichloromethane. The methanolysis gave a methyl ether corresponding to the starting chloride, as a result of capture of the intermediate Cp cation by a solvent molecule, whereas under the latter conditions the Cp cation underwent Wagner-Meerwein rearrangement of the homoadamantene framework to avoid antiaromatic destabilization and subsequent intramolecular cyclopropanation, giving a stable allyl cation.

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Details 詳細情報について

  • CRID
    1390282680530618624
  • NII Article ID
    130004646356
  • DOI
    10.11494/kisoyuki.55.0.24.0
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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