Iwata Takayuki, Kawano Ryusei, Fukami Takuto, Shindo Mitsuru
Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasuga-koen, Kasuga, 816-8580, Japan.
Interdisciplinary Graduate School of Engineering Sciences, Kyushu University, 6-1 Kasuga-koen, Kasuga, 816-8580, Japan.
Chemistry. 2022 Feb 24;28(12):e202104160. doi: 10.1002/chem.202104160. Epub 2022 Feb 3.
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.
通过在酸性条件下使用逆傅克反应类型的反应使三蝶烯骨架开环，得到其相应的蒽酮产物。9-羟基三蝶烯和未取代的三蝶烯在强酸性条件下，如与三氟甲磺酸反应时会发生开环反应。对取代效应的研究表明，芳烃部分上的供电子基团使得反应能够在较弱的酸（如三氟乙酸）存在下进行。此外，该反应已成功应用于并四苯的合成。
