Anthranoxides as Highly Reactive Arynophiles for the Synthesis of Triptycenes |
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| Authors: | Dr Takayuki Iwata Mizuki Hyodo Takuto Fukami Prof?Dr Yoshihito Shiota Prof?Dr Kazunari Yoshizawa Prof?Dr Mitsuru Shindo |
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| Institution: | 1. Institute for Materials Chemistry and Engineering, Kyushu University, Kasuga-koen, Kasuga, 816-8580 Japan;2. Interdisciplinary Graduate School of Engineering Sciences, Kyushu University, Kasuga-koen, Kasuga, 816-8580 Japan |
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| Abstract: | We report herein an efficient method to synthesize triptycenes by the reaction of benzynes and anthranoxides, which are electron-rich and readily prepared from the corresponding anthrones. Using this method, 1,9-syn-substituted triptycenes were regioselectively obtained employing 3-methoxybenzynes. This method was also applied to synthesize pentiptycenes. A DFT study revealed that the cycloaddition of lithium anthranoxide and benzyne proceeds stepwise. |
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| Keywords: | anthracene benzyne cycloaddition DFT triptycene |
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