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dc.contributor.authorCristol, Stanleyen_US
dc.contributor.authorMorrill, Terenceen_US
dc.contributor.authorSanchez, Roberten_US
dc.identifier.citationJournal of the American Chemical Society 88N13 (1966) 3087-3090en_US
dc.description.abstractexo-3-Deuteriodehydro-2-norbornyl p-bromobenzenesulfonate (VIIb) solvolyzes in glacial acetic acid to give about 7 % of an equimolar mixture of exo-3-deuteriodehydro-2-norbornyl acetate (VIId) and 7-deuteriodehydro-2-norbornyl acetate (VIIId), along with about 93 % of deuterated 3-nortricyclyl acetate (IId). The acetolysis is accompanied by a considerably more rapid scrambling of the p-bromobenzenesulfonate by internal return to 7-deuteriodehydro-2-norbornyl p-bromobenzenesulfonate (VIIIb), without attendant formation of deuterated nortricyclyl p-bromobenzenesulfonate (IIb). The data are consistent with the assumption that ion pairs involving a symmetrical nonclassical cation such as IV are produced in the ionization process, or with the assumption that rapidly equilibrating nonsymmetrical cations such as V and VI are involved, but are not consistent with the suggestion made earlier that the nonsymmetrical cation V is formed in the ionization step and isomerizes relatively slowly to its Wagner-Meerwein isomer VI.en_US
dc.format.extent31371 bytesen_US
dc.publisherAmerican Chemical Society: Journal of the American Chemical Societyen_US
dc.relation.ispartofseriesBridged Polycyclic Compoundsen_US
dc.subjectNonsymmetrical cation Ven_US
dc.subjectWagner-Meerwein isomer VIen_US
dc.titleRearrangements in the acetolysis of exo-dehydro-2-norbornyl p-bromobenzenesulfonateen_US

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