2017年3月
Facile Synthesis of Polycyclic Pentalenes with Enhanced Huckel Antiaromaticity
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- ,
- ,
- 巻
- 56
- 号
- 12
- 開始ページ
- 3270
- 終了ページ
- 3274
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1002/anie.201611344
- 出版者・発行元
- WILEY-V C H VERLAG GMBH
Pentalenes represent highly reactive Huckel antiaromatics with 8 pi electrons. Usually, pentalenes are stabilized by incorporation of two benzene rings in a fused fashion. In dibenzo[a,e]pentalenes, however, the high aromaticity of the fused benzene rings compromises the inherent antiaromaticity of the pentalene core. Herein, we disclose that this forfeited antiaromaticity can be restored by fusing four additional aromatic rings onto the peripheral positions of dibenzo[ a, e]pentalenes. Such polycyclic pentalenes were prepared by successive transannular cyclizations via in situ-generated tetrakisdehydro[16]annulenes. The thus obtained compounds showed intriguing properties, for example, characteristic absorptions in the visible-to-near-infrared (NIR) region and low reduction potentials. These results hence afford a design principle to produce highly antiaromatic yet stable pentalenes. The antiaromaticity of the pentalene core can be widely tuned via the degree of aromaticity of the peripherally fused rings.
- リンク情報
- ID情報
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- DOI : 10.1002/anie.201611344
- ISSN : 1433-7851
- eISSN : 1521-3773
- Web of Science ID : WOS:000397329300025