dc.date.accessioned | 2018-09-11T13:10:21Z | |
dc.date.available | 2019-06-14T22:47:15Z | |
dc.date.created | 2018-06-21T11:29:13Z | |
dc.date.issued | 2018 | |
dc.identifier.citation | Nishiyama, Akihide Fukuda, Masaya Mori, Shigeki Furukawa, Ko Fliegl, Heike Furuta, Hiroyuki Shimizu, Soji . First Rational Synthesis of Antiaromatic 5,15‐Dioxaporphyrin and Its β,β‐Linked Dimer Formation upon Oxidation. Angewandte Chemie International Edition. 2018 | |
dc.identifier.uri | http://hdl.handle.net/10852/64627 | |
dc.description.abstract | 5,15‐Dioxaporphyrin was synthesized for the first time by a nucleophilic aromatic substitution reaction of a nickel bis(α,α′‐dibromodipyrrin) complex with benzaldoxime, followed by an intramolecular annulation of the α‐hydroxy‐substituted intermediate. This unprecedented molecule is a 20π‐electron antiaromatic system, in terms of Hückel's rule of aromaticity, because lone pair electrons of oxygen atoms are incorporated into the 18π‐electron conjugated system of the porphyrin. A theoretical analysis based on the gauge‐including magnetically induced current method confirmed its antiaromaticity and a dominant inner ring pathway for the ring current. The unique reactivity of 5,15‐dioxaporphyrin forming a β,β‐linked dimer upon oxidation was also revealed.
© 2018 Wiley | en_US |
dc.language | EN | |
dc.publisher | Wiley - VCH Verlag GmbH | |
dc.title | First Rational Synthesis of Antiaromatic 5,15‐Dioxaporphyrin and Its β,β‐Linked Dimer Formation upon Oxidation | en_US |
dc.title.alternative | ENEngelskEnglishFirst Rational Synthesis of Antiaromatic 5,15‐Dioxaporphyrin and Its β,β‐Linked Dimer Formation upon Oxidation | |
dc.type | Journal article | |
dc.creator.author | Nishiyama, Akihide | |
dc.creator.author | Fukuda, Masaya | |
dc.creator.author | Mori, Shigeki | |
dc.creator.author | Furukawa, Ko | |
dc.creator.author | Fliegl, Heike | |
dc.creator.author | Furuta, Hiroyuki | |
dc.creator.author | Shimizu, Soji | |
cristin.unitcode | 185,15,12,70 | |
cristin.unitname | Hylleraas-senteret | |
cristin.ispublished | true | |
cristin.fulltext | original | |
cristin.qualitycode | 2 | |
dc.identifier.cristin | 1592868 | |
dc.identifier.bibliographiccitation | info:ofi/fmt:kev:mtx:ctx&ctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Angewandte Chemie International Edition&rft.volume=&rft.spage=&rft.date=2018 | |
dc.identifier.jtitle | Angewandte Chemie International Edition | |
dc.identifier.doi | http://dx.doi.org/10.1002/anie.201804648 | |
dc.identifier.urn | URN:NBN:no-67164 | |
dc.type.document | Tidsskriftartikkel | |
dc.type.peerreviewed | Peer reviewed | |
dc.source.issn | 1433-7851 | |
dc.identifier.fulltext | Fulltext https://www.duo.uio.no/bitstream/handle/10852/64627/2/Nishiyama_et_al-2018-Angewandte_Chemie_International_Edition.pdf | |
dc.type.version | PublishedVersion | |
dc.relation.project | NFR/231571 | |
dc.relation.project | NFR/262695 | |
dc.relation.project | NOTUR/NORSTORE/NN4654K | |