Anthranoxides as Highly Reactive Arynophiles for Synthesis of Triptycenes

• Iwata, Takayuki

  Institute for Materials Chemistry and Engineering, Kyushu University

• Hyodo, Mizuki

  Interdisciplinary Graduate School of Engineering Sciences, Kyushu University

• Fukami, Takuto

  Interdisciplinary Graduate School of Engineering Sciences, Kyushu University

• Shiota, Yoshihito

  Institute for Materials Chemistry and Engineering, Kyushu University

• Yoshizawa, Kazunari

  Institute for Materials Chemistry and Engineering, Kyushu University

• Shindo, Mitsuru

  Institute for Materials Chemistry and Engineering, Kyushu University

Bibliographic Information

Other Title

• Anthranoxides as Highly Reactive Arynophiles for the Synthesis of Triptycenes

Abstract

We report herein an efficient method to synthesize triptycenes by the reaction of benzynes and anthranoxides, which are electron-rich and readily prepared from the corresponding anthrones. Using this method, 1,9-syn-substituted triptycenes were regioselectively obtained employing 3-methoxybenzynes. This method was also applied to synthesize pentiptycenes. A DFT study revealed that the cycloaddition of lithium anthranoxide and benzyne proceeds stepwise.

Dedicated to Professor Koichi Fukase on the occasion of his 60th birthday

Journal

• Chemistry A European Journal

  Chemistry A European Journal 26 (39), 8506-8510, 2020-05-20

  Wiley

Keywords

• triptycene
• anthracene
• benzyne
• cycloaddition

Details

• CRID: 1050580007680299392
• NII Article ID: 120007187862
• NII Book ID: AA11076269
• DOI: 10.1002/chem.202002065
• ISSN: 15213765
• ISSN: 09476539
• HANDLE: 2324/4752569
• Web Site: https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchem.202002065
• Web Site: https://onlinelibrary.wiley.com/doi/pdf/10.1002/chem.202002065
• Web Site: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/chem.202002065
• Text Lang: en
• Article Type: journal article
• Data Source:
  • IRDB
  • Crossref
  • CiNii Articles
  • KAKEN