Anthranoxides as Highly Reactive Arynophiles for the Synthesis of Triptycenes

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....

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Bibliographic Details
Published in:Chemistry : a European journal 2020-07, Vol.26 (39), p.8506-8510
Main Authors: Iwata, Takayuki, Hyodo, Mizuki, Fukami, Takuto, Shiota, Yoshihito, Yoshizawa, Kazunari, Shindo, Mitsuru
Format: Article
Language:English
Subjects:
anthracene
benzyne
Chemistry
Cycloaddition
DFT
Lithium
triptycene
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Summary: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. An efficient method to synthesize triptycenes is reported by the reaction of benzynes and anthranoxides, which are electron‐rich and readily prepared from the corresponding anthrones (see scheme). 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.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202002065