This study finds that triptycenes can undergo ring opening solely after acid treatment. Triptycenes have ar igid and stable framework that enables them to act as the core structure for multifunctional molecules. Thus, their skeletal transformation is unusual and remains untapped in organic synthesis. We have found that ring opening of the triptycene scaffold occurs under acidic conditions in ar etro-Friedel-Crafts fashion to give the corresponding anthrone product. This simple yet overlooked reaction allows triptycene to serve as a" reactive unit". We also used this ring-opening reaction to synthesize tetracene, further demonstrating the potential of the reaction for the preparation of functionalized acenes.
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.
The triptycene scaffold has been ring‐opened by using an acidic retro‐Friedel‐Crafts‐type reaction to give its corresponding anthrone product. 9‐Hydroxytriptycenes and unsubstituted triptycene were ring‐opened by treatment with TfOH. The electron‐donating group on the arene moiety allows the reaction to proceed in the presence of weaker acids. Additionally, the reaction has been applied toward the synthesis of tetracene. More information can be found in the Research Article by T. Iwata, M. Shindo et al. (DOI: 10.1002/chem.202104160).
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