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Exploiting Imine Photochemistry for Masked N‐Centered Radical Reactivity
dc.contributor.authorStaveness, Daryl
dc.contributor.authorCollins, James L.
dc.contributor.authorMcAtee, Rory C.
dc.contributor.authorStephenson, Corey R. J.
dc.date.accessioned2020-01-13T15:05:31Z
dc.date.availableWITHHELD_12_MONTHS
dc.date.available2020-01-13T15:05:31Z
dc.date.issued2019-12-19
dc.identifier.citationStaveness, Daryl; Collins, James L.; McAtee, Rory C.; Stephenson, Corey R. J. (2019). "Exploiting Imine Photochemistry for Masked N‐Centered Radical Reactivity." Angewandte Chemie 131(52): 19176-19182.
dc.identifier.issn0044-8249
dc.identifier.issn1521-3757
dc.identifier.urihttps://hdl.handle.net/2027.42/152593
dc.description.abstractThis report details the development of a masked N‐centered radical strategy that harvests the energy of light to drive the conversion of cyclopropylimines to 1‐aminonorbornanes. This process employs the N‐centered radical character of a photoexcited imine to facilitate the homolytic fragmentation of the cyclopropane ring and the subsequent radical cyclization sequence that forms two new C−C bonds en route to the norbornane core. Achieving bond‐forming reactivity as a function of the N‐centered radical character of an excited state Schiff base is unique, requiring only violet light in this instance. This methodology operates in continuous flow, enhancing the potential to translate beyond the academic sector. The operational simplicity of this photochemical process and the structural novelty of the (hetero)aryl‐fused 1‐aminonorbornane products are anticipated to provide a valuable addition to discovery efforts in pharmaceutical and agrochemical industries.Der N‐zentrierte offenschalige Charakter von photoangeregten Cyclopropyliminen wird genutzt, um eine radikalische Fragmentierungs‐ und Cyclisierungssequenz einzuleiten, die Brückenkopf‐funktionalisierte Norbornane erzeugt. Diese einzigartige Reaktivität benötigt lediglich violettes Licht, und die 1‐Aminonorbornan‐Produkte sind wertvolle Bausteine für die Entdeckung von Wirkstoffen und Agrochemikalien.
dc.publisherCRC Press
dc.publisherWiley Periodicals, Inc.
dc.subject.otherAngeregter Zustand
dc.subject.other1-Aminonorbornan
dc.subject.otherCyclopropylimin
dc.subject.otherImin-Photochemie
dc.subject.otherN-zentrierte Radikale
dc.titleExploiting Imine Photochemistry for Masked N‐Centered Radical Reactivity
dc.typeArticle
dc.rights.robotsIndexNoFollow
dc.subject.hlbsecondlevelChemical Engineering
dc.subject.hlbsecondlevelChemistry
dc.subject.hlbsecondlevelMaterials Science and Engineering
dc.subject.hlbtoplevelEngineering
dc.subject.hlbtoplevelScience
dc.description.peerreviewedPeer Reviewed
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/152593/1/ange201909492.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/152593/2/ange201909492_am.pdf
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/152593/3/ange201909492-sup-0001-misc_information.pdf
dc.identifier.doi10.1002/ange.201909492
dc.identifier.sourceAngewandte Chemie
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dc.owningcollnameInterdisciplinary and Peer-Reviewed


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