Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 28, Issue 12, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202104160
Keywords
anthrones; acenes; retro-Friedel-Crafts reaction; ring-opening reaction; triptycenes
Categories
Funding
- JSPS KAKENHI [JP18H02557, JP18H04418, JP18H04624, JP20H04780, JP20K21198, JP20K15283]
- NAGASE Science Technology Foundation
- Asahi Glass Foundation
- Qdai-jump Research Program Wakaba Challenge at Kyushu University
- IRCCS Fusion Emergent Research Program
- IMCE, Kyushu university
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The triptycene scaffold can be ring-opened through a retro-Friedel-Crafts-type reaction under acidic conditions, yielding the corresponding anthrone product. 9-Hydroxytriptycenes and unsubstituted triptycene undergo ring-opening reaction in strongly acidic conditions, such as with TfOH. The investigation of the substitution effect reveals that an electron-donating group on the arene moiety allows the reaction to proceed in the presence of a weaker acid, such as TFA. Additionally, the reaction has proven successful for the synthesis of tetracene.
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.
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