dc.contributor.author | Cristol, Stanley | en_US |
dc.contributor.author | Morrill, Terence | en_US |
dc.contributor.author | Sanchez, Robert | en_US |
dc.date.accessioned | 2006-07-19T18:37:51Z | en_US |
dc.date.available | 2006-07-19T18:37:51Z | en_US |
dc.date.issued | 1966-07-05 | en_US |
dc.identifier.citation | Journal of the American Chemical Society 88N13 (1966) 3087-3090 | en_US |
dc.identifier.issn | 1520-5126 | en_US |
dc.identifier.uri | http://hdl.handle.net/1850/2136 | en_US |
dc.description.abstract | exo-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.extent | 31371 bytes | en_US |
dc.format.mimetype | application/pdf | en_US |
dc.language.iso | en_US | en_US |
dc.publisher | American Chemical Society: Journal of the American Chemical Society | en_US |
dc.relation.ispartofseries | Bridged Polycyclic Compounds | en_US |
dc.relation.ispartofseries | XXXVI | en_US |
dc.subject | Nonsymmetrical cation V | en_US |
dc.subject | Wagner-Meerwein isomer VI | en_US |
dc.title | Rearrangements in the acetolysis of exo-dehydro-2-norbornyl p-bromobenzenesulfonate | en_US |
dc.type | Abstract | en_US |
dc.identifier.url | http://dx.doi.org/10.1021/ja00965a036 | |