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- Title
Carbon Participation in the Solvolysis of 6- endo-Substituted 2- exo-Norbornyl Toluenesulfonates. Norbornanes part 6.
- Authors
Grob, Cyril A.; Günther, Bettina; Hanreich, Reinhard
- Abstract
The solvolysis rate constants k for the 6- endo-substituted 2- exo-norbornyl toluenesulfonates 7 have been determined. Values of log k correlate well with the respective inductive constants of the substitutents except when the latter are nucleophilic and therefore lead to endo-cyclization, or when they are n-electron donors and cause concerted fragmentation. In general 6- endo-substituted tosylates 7 react somewhat more slowly than their 6- exo-epimers. Identical or different mixtures were obtained from the C(6)-epimers 7 and 1 depending on whether the substituent was an electron donor or acceptor. It is concluded that donor substituents at C(6) enhance 1,3-bridging in the intermediate epimeric cations and lead to their rapid and complete equilibration, and that electron acceptors reduce bridging and hence their equilibration rates.
- Publication
Helvetica Chimica Acta, 1981, Vol 64, Issue 7, p2312
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19810640736