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2-(3-Pyrrolin-1-yl)-1,4-naphthoquinones: Photoactivated Alkylating Agents
dc.contributor.authorAponick, Aaronen_US
dc.contributor.authorDietz, Amber L.en_US
dc.contributor.authorPearson, William H.en_US
dc.date.accessioned2008-10-01T15:22:27Z
dc.date.available2009-10-02T17:27:37Zen_US
dc.date.issued2008-09en_US
dc.identifier.citationAponick, Aaron; Dietz, Amber L.; Pearson, William H. (2008). "2-(3-Pyrrolin-1-yl)-1,4-naphthoquinones: Photoactivated Alkylating Agents." European Journal of Organic Chemistry 2008(25): 4264-4276. <http://hdl.handle.net/2027.42/60962>en_US
dc.identifier.issn1434-193Xen_US
dc.identifier.issn1099-0690en_US
dc.identifier.urihttps://hdl.handle.net/2027.42/60962
dc.description.abstractThe preparation of 2-(3-pyrrolin-1-yl)-1,4-naphthoquinones and a study of their use as photoactivated alkylating agents is reported. The title compounds were easily synthesized by conjugate addition of the corresponding 3-pyrrolines to various naphthoquinones. Upon exposure to ambient room light, the compounds undergo an internal redox reaction to form 2-(pyrrol-1-yl)-1,4-hydroquinones, which are activated for nucleophilic addition by an S N 1 azafulvene mechanism. Control experiments demonstrated that the redox reaction is triggered by light and that the nucleophilic addition does not proceed before this activation occurs.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)en_US
dc.format.extent367300 bytes
dc.format.extent3118 bytes
dc.format.mimetypeapplication/pdf
dc.format.mimetypetext/plain
dc.publisherWILEY-VCH Verlagen_US
dc.subject.otherChemistryen_US
dc.subject.otherGeneral Chemistryen_US
dc.title2-(3-Pyrrolin-1-yl)-1,4-naphthoquinones: Photoactivated Alkylating Agentsen_US
dc.typeArticleen_US
dc.rights.robotsIndexNoFollowen_US
dc.subject.hlbsecondlevelBiological Chemistryen_US
dc.subject.hlbsecondlevelChemical Engineeringen_US
dc.subject.hlbsecondlevelChemistryen_US
dc.subject.hlbsecondlevelMaterials Science and Engineeringen_US
dc.subject.hlbtoplevelHealth Sciencesen_US
dc.subject.hlbtoplevelScienceen_US
dc.subject.hlbtoplevelEngineeringen_US
dc.description.peerreviewedPeer Revieweden_US
dc.contributor.affiliationumDepartment of Chemistry, University of Michigan, Ann Arbor, MI 48109-1055, USA ; Current address: Department of Chemistry, University ofFlorida,Gainesville, FL 32611, USA, Fax: +1-352-846-0296 ;en_US
dc.contributor.affiliationumDepartment of Chemistry, University of Michigan, Ann Arbor, MI 48109-1055, USAen_US
dc.contributor.affiliationumDepartment of Chemistry, University of Michigan, Ann Arbor, MI 48109-1055, USA ; Current address: Berry & Associates, Inc.,2434 Bishop Circle East, Dexter, MI 48130, USAen_US
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/60962/1/4264_ftp.pdf
dc.identifier.doihttp://dx.doi.org/10.1002/ejoc.200800482en_US
dc.owningcollnameInterdisciplinary and Peer-Reviewed


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