dc.contributor.author | Kancherla, Sindhu | |
dc.contributor.author | Lorentzen, Marianne | |
dc.contributor.author | Snieckus, Victor | |
dc.contributor.author | Jørgensen, Kåre Bredeli | |
dc.date.accessioned | 2021-05-26T13:27:34Z | |
dc.date.available | 2021-05-26T13:27:34Z | |
dc.date.created | 2018-11-23T12:27:54Z | |
dc.date.issued | 2018-03 | |
dc.identifier.citation | Kancherla, S., Lorentzen, M., Snieckus, V., Jørgensen, K.B. (2018) Directed ortho-Metalation and Anionic ortho-Fries Rearrangement of Polycyclic Aromatic O-Carbamates: Regioselective Synthesis of Substituted Chrysenes. Journal of Organic Chemistry, 83(7), 3590-3598. | en_US |
dc.identifier.issn | 0022-3263 | |
dc.identifier.uri | https://hdl.handle.net/11250/2756486 | |
dc.description | This document is the Accepted Manuscript version of a Published Work that appeared in final form in the Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.7b03210. | en_US |
dc.description.abstract | A general method for the regioselective synthesis of a series of ortho-substituted chrysenyl N,N-diethyl-O-carbamates by the directed ortho-metalation (DoM) strategy is reported. The starting O-carbamates were prepared from the corresponding chrysenols, available by oxidative photochemical cyclization or directed remote metalation tactics. Chrysen-1-yl and chrysene-3-yl ring site selectivity of directed ortho-metalation (DoM) and anionic ortho-Fries rearrangement (AoF) protocols, with s-BuLi/TMEDA, followed by electrophilic quench using a selection of electrophiles, were observed, leading to new chrysenyl derivatives. 5-Chrysenyl N,N-diethyl-O-carbamate underwent instant AoF rearrangement even at −100 °C to furnish chrysenyl o-hydroxycarboxamide. Iterative DoM reactions were carried out to gain insight into the regioselectivity factors. | en_US |
dc.language.iso | eng | en_US |
dc.publisher | American Chemical Society | en_US |
dc.subject | kjemi | en_US |
dc.title | Directed ortho-Metalation and Anionic ortho-Fries Rearrangement of Polycyclic Aromatic O-Carbamates: Regioselective Synthesis of Substituted Chrysenes | en_US |
dc.type | Peer reviewed | en_US |
dc.type | Journal article | en_US |
dc.description.version | acceptedVersion | en_US |
dc.rights.holder | © American Chemical Society 2018 | en_US |
dc.subject.nsi | VDP::Matematikk og Naturvitenskap: 400::Kjemi: 440::Organisk kjemi: 441 | en_US |
dc.source.pagenumber | 3590-3598 | en_US |
dc.source.volume | 83 | en_US |
dc.source.journal | Journal of Organic Chemistry | en_US |
dc.source.issue | 7 | en_US |
dc.identifier.doi | 10.1021/acs.joc.7b03210 | |
dc.identifier.cristin | 1634248 | |
cristin.ispublished | true | |
cristin.fulltext | postprint | |
cristin.qualitycode | 2 | |