Retro-Friedel-Crafts-Type Acidic Ring-Opening of Triptycenes: A New Synthetic Approach to Acenes |
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| Authors: | Dr Takayuki Iwata Ryusei Kawano Takuto Fukami Prof Dr Mitsuru Shindo |
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| Institution: | 1. Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasuga-koen, Kasuga, 816-8580 Japan;2. Interdisciplinary Graduate School of Engineering Sciences, Kyushu University, 6-1 Kasuga-koen, Kasuga, 816-8580 Japan |
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| 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. |
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| Keywords: | anthrones acenes retro-Friedel-Crafts reaction ring-opening reaction triptycenes |
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