dc.contributor.author | Tiruye, Hiwot Minwuyelet | |
dc.contributor.author | Jørgensen, Kåre Bredeli | |
dc.date.accessioned | 2023-03-15T13:25:52Z | |
dc.date.available | 2023-03-15T13:25:52Z | |
dc.date.created | 2022-12-13T13:29:41Z | |
dc.date.issued | 2022 | |
dc.identifier.citation | Tiruye, H. M., & Jørgensen, K. B. (2022). Oxidative synthesis of ortho-quinones from hydroxy-PAHs by stabilized formulation of 2-iodoxybenzoic acid (SIBX). Tetrahedron, 129, 133144. | en_US |
dc.identifier.issn | 0040-4020 | |
dc.identifier.uri | https://hdl.handle.net/11250/3058476 | |
dc.description.abstract | Polycyclic aromatic phenols (PAPs or hydroxy-PAHs) are conveniently converted into their corresponding ortho-quinones using commercially available stabilized iodoxybenzoic acid (SIBX). SIBX provides a safer and commercially available alternative to IBX and displays the same selectivity with comparable or better yields in the oxidative dearomatization of phenols to ortho-quinone, including examples where formation of para-quinones is feasible. This ortho-selectivity from all positions of a hydroxy-group allowed for simple synthesis of the prerequisite hydroxy-PAHs by either photochemical cyclization of stilbenes or Pt-catalyzed cycloisomerization. The later synthesis involved a four-step sequence where suitably substituted biphenyls were prepared by Suzuki-Miyaura cross-coupling, followed by the Corey–Fuchs protocol and cycloisomerization by a catalytic amount of PtCl2. 2- and 4-methylphenanthene were also prepared for the first time using this method. | en_US |
dc.language.iso | eng | en_US |
dc.publisher | Elsevier | en_US |
dc.rights | Navngivelse 4.0 Internasjonal | * |
dc.rights.uri | http://creativecommons.org/licenses/by/4.0/deed.no | * |
dc.title | Oxidative synthesis of ortho-quinones from hydroxy-PAHs by stabilized formulation of 2-iodoxybenzoic acid (SIBX) | en_US |
dc.type | Peer reviewed | en_US |
dc.type | Journal article | en_US |
dc.description.version | publishedVersion | en_US |
dc.rights.holder | The authors | en_US |
dc.subject.nsi | VDP::Teknologi: 500 | en_US |
dc.subject.nsi | VDP::Matematikk og Naturvitenskap: 400::Kjemi: 440 | en_US |
dc.source.journal | Tetrahedron | en_US |
dc.identifier.doi | 10.1016/j.tet.2022.133144 | |
dc.identifier.cristin | 2092566 | |
cristin.ispublished | true | |
cristin.fulltext | original | |
cristin.qualitycode | 1 | |