Retro-Friedel-Crafts-Type Acidic Ring-Opening of Triptycenes: A New Synthetic Approach to Acenes

Takayuki Iwata, Ryusei Kawano, Takuto Fukami, Mitsuru Shindo

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

The triptycene scaffold has been ring-opened by using a retro-Friedel-Crafts-type reaction under acidic conditions to give its corresponding anthrone product. 9-Hydroxytriptycenes and unsubstituted triptycene undergo ring-opening reaction under strongly acidic conditions, such as with TfOH. An investigation of the substitution effect has revealed that the electron-donating group on the arene moiety allows the reaction to proceed in the presence of a weaker acid, such as TFA. In addition, the reaction has been successfully applied toward the synthesis of tetracene.

Original languageEnglish
Article numbere202104160
JournalChemistry - A European Journal
Volume28
Issue number12
DOIs
Publication statusPublished - Feb 24 2022

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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