2012年10月
Retro-Diels-Alder approach to the synthesis of π-expanded azuliporphyrins and their porphyrinoid aromaticity
Chemistry - A European Journal
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- 巻
- 18
- 号
- 40
- 開始ページ
- 12854
- 終了ページ
- 12863
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1002/chem.201201399
Bicyclo[2.2.2]octadiene (BCOD) fused azuliporphyrins were synthesized by 3+1 porphyrin synthesis of azulitripyrranes with diformylpyrroles. Subsequent retro-Diels-Alder reaction of the BCOD-fused azuliporphyrins afforded azulibenzo-, azulidibenzo-, and azulitribenzoporphyrins 1-5. NMR and UV/Vis spectra, as well as nucleus-independent chemical shift (NICS) calculations revealed that 1-5 and their diprotonated dications exhibit relatively low porphyrinoid aromaticity, which was dependent on the position and number of fused benzene rings present. Porphyrins: A series of azulibenzoporphyrins were synthesized based on 3+1 porphyrin synthesis and retro-Diels-Alder reaction of bicyclo[2.2.2] octadiene-fused precursors (see scheme). UV/Vis spectra and NICS calculations revealed that their diprotonated dications exhibited a low porphyrinoid aromaticity from the porphyrinlike π circuit, which was dependent on the position and number of fused benzene rings. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
- リンク情報
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- DOI
- https://doi.org/10.1002/chem.201201399
- Web of Science
- https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000309238400037&DestApp=WOS_CPL
- URL
- https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84867043681&origin=inward
- ID情報
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- DOI : 10.1002/chem.201201399
- ISSN : 0947-6539
- eISSN : 1521-3765
- SCOPUS ID : 84867043681
- Web of Science ID : WOS:000309238400037