dc.contributor.author | Busfield, WK | |
dc.contributor.author | Byriel, KA | |
dc.contributor.author | Grice, ID | |
dc.contributor.author | Jenkins, ID | |
dc.contributor.author | Lynch, DE | |
dc.date.accessioned | 2017-06-27T01:30:28Z | |
dc.date.available | 2017-06-27T01:30:28Z | |
dc.date.issued | 2000 | |
dc.date.modified | 2007-07-27T02:05:36Z | |
dc.identifier.issn | 0300-9580 | |
dc.identifier.doi | 10.1039/A908455J | |
dc.identifier.uri | http://hdl.handle.net/10072/3448 | |
dc.description.abstract | The 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. | |
dc.description.peerreviewed | Yes | |
dc.description.publicationstatus | Yes | |
dc.language | English | |
dc.language.iso | eng | |
dc.publisher | Royal Society of Chemistry | |
dc.publisher.place | UK | |
dc.publisher.uri | http://www.rsc.org/delivery/_ArticleLinking/ArticleLinking.cfm?JournalCode=P2&Year=2000&ManuscriptID=a908455j&Iss=4 | |
dc.relation.ispartofpagefrom | 757 | |
dc.relation.ispartofpageto | 760 | |
dc.relation.ispartofjournal | Journal of the Chemical Society. Perkin Transactions 2 | |
dc.relation.ispartofvolume | 2000 | |
dc.subject.fieldofresearch | History, heritage and archaeology | |
dc.subject.fieldofresearchcode | 43 | |
dc.title | The stereoselectivity of addition of benzoyloxyl radicals to trans-A2-octalin | |
dc.type | Journal article | |
dc.type.description | C1 - Articles | |
dc.type.code | C - Journal Articles | |
gro.faculty | Griffith Sciences, School of Natural Sciences | |
gro.rights.copyright | © 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. | |
gro.date.issued | 2000 | |
gro.hasfulltext | No Full Text | |
gro.griffith.author | Jenkins, Ian D. | |
gro.griffith.author | Grice, Darren D. | |