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dc.contributor.authorBusfield, Kenen_US
dc.contributor.authorByriel, Karl A.en_US
dc.contributor.authorGrice, Darrenen_US
dc.contributor.authorJenkins, Ianen_US
dc.contributor.authorE. Lynch, Danielen_US
dc.date.accessioned2017-06-27T01:30:28Z
dc.date.available2017-06-27T01:30:28Z
dc.date.issued2000en_US
dc.date.modified2007-07-27T02:05:36Z
dc.identifier.issn1472779Xen_US
dc.identifier.doi10.1039/A908455Jen_AU
dc.identifier.urihttp://hdl.handle.net/10072/3448
dc.description.abstractThe stereochemistry of addition of benzoyloxyl radicals to the conformationally rigid cyclohexene, trans-2-octalin, in the presence of the free radical scavenger 1,1,3,3-tetramethyl-2,3-dihydro-1H-isoindol-2-yloxyl, is reported. Axial addition was favoured over equatorial addition with modest selectivity (axialequatorial = 1.71.0). The aminoxyl trapping reaction was more selective with a ratio of transcis addition of 4.41.0. Interestingly, when the benzoate group is axial, axial trapping by the sterically hindered aminoxyl is strongly favoured (axialequatorial = 7.41.0), whereas when the benzoate group is equatorial, there is only a small preference for equatorial trapping by the aminoxyl (equatorialaxial = 2.41.0). The structures of the four possible addition products were determined by 1H and 13C NMR spectroscopy, and confirmed in the case of the diaxial addition product [2(ax)-benzoyloxy-3(ax)-(1,1,3,3-tetramethyl-2,3-dihydroisoindol-2-yloxy)-trans-decalin 3] by X-ray crystallographic analysis.en_US
dc.description.peerreviewedYesen_US
dc.description.publicationstatusYesen_AU
dc.languageEnglishen_US
dc.language.isoen_AU
dc.publisherRoyal Society of Chemistryen_US
dc.publisher.placeUKen_US
dc.publisher.urihttp://www.rsc.org/delivery/_ArticleLinking/ArticleLinking.cfm?JournalCode=P2&Year=2000&ManuscriptID=a908455j&Iss=4en_AU
dc.relation.ispartofpagefrom757en_US
dc.relation.ispartofpageto760en_US
dc.relation.ispartofjournalJournal of the Chemical Society. Perkin Transactions 2en_US
dc.relation.ispartofvolume2000en_US
dc.subject.fieldofresearchHISTORY AND ARCHAEOLOGYen_US
dc.subject.fieldofresearchcode210000en_US
dc.subject.fieldofresearchcode250301en_US
dc.titleThe stereoselectivity of addition of benzoyloxyl radicals to trans-A2-octalinen_US
dc.typeJournal articleen_US
dc.type.descriptionC1 - Peer Reviewed (HERDC)en_US
dc.type.codeC - Journal Articlesen_US
gro.facultyGriffith Sciences, School of Natural Sciencesen_US
gro.rights.copyrightCopyright 2000 Royal Society of Chemistry. This is the author-manuscript version of this paper. Please refer to the journal link for access to the definitive, published version.en_AU
gro.date.issued2000
gro.hasfulltextNo Full Text


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