2016年7月
Double Ring Expansion from an Aromatic [18]Porphyrin(1.1.1.1) to an Antiaromatic [20]Porphyrin(2.1.2.1)
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
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- 巻
- 55
- 号
- 28
- 開始ページ
- 8095
- 終了ページ
- 8099
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1002/anie.201602874
- 出版者・発行元
- WILEY-V C H VERLAG GMBH
Double ring expansion from a 5,15-diarylporphyrin to a 5,16-diaryl-10,11,21,22-tetradehydro[20]porphyrin(2.1.2.1) occurred through a reaction sequence consisting of oxidation with PbO2 to 5,15-dioxoporphodimethene, a CoreyFuchs reaction with tetrabromomethane in the presence of triphenylphosphine, and Fritsch-Buttenberg-Wiechell rearrangement triggered by tert-butyllithium. The obtained tetradehydro[20]porphyrin(2.1.2.1) and its mono-and dihydrogenated congeners exhibited 20 pi antiaromatic character, whereas overhydrogenated congeners bearing a saturated bridge were nonaromatic owing to disrupted pi conjugation.
- リンク情報
- ID情報
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- DOI : 10.1002/anie.201602874
- ISSN : 1433-7851
- eISSN : 1521-3773
- Web of Science ID : WOS:000383253100039