The stereoselectivity of addition of benzoyloxyl radicals to trans-A2-octalin

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Title The stereoselectivity of addition of benzoyloxyl radicals to trans-A2-octalin
Author Busfield, Walter Kenneth; Byriel, Karl A.; Grice, Darren; Jenkins, Ian Douglas; Lynch, Daniel E.
Journal Name Journal of the Chemical Society. Perkin Transactions 2
Year Published 2000
Place of publication UK
Publisher Royal Society of Chemistry
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.
Peer Reviewed Yes
Published Yes
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Copyright Statement 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.
Volume N/A
Page from 757
Page to 760
ISSN 1472-779X
Date Accessioned 2001-01-01
Language en_AU
Research Centre Institute for Glycomics
Faculty Faculty of Science
Subject Organic Chemical Synthesis; Science & Technology
Publication Type Article in Scholarly Refereed Journal
Publication Type Code c1

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