75305-52-1Relevant articles and documents
POLAR AND ANCHIMERIC EFFECTS IN THE SOLVOLYSIS OF 6-endo-SUBSTITUTED 2-NORBORNYL-p-TOLUENE-SULFONATES
Grob, Cyril A.,Guenther, Bettina,Hanreich, Reinhard
, p. 1211 - 1214 (1981)
A study of the influence of 6-endo substituents on the reactivity of 2-exo- and 2-endo-norbornyl p-toluenesulfonates 3 and 4, respectively, confirms that polar rather than steric effects control relative rates.
Synthese und Hydrolyse von 6endo-substituierten p-Toluolsulfonsaeure-estern.
Grob, Cyril A.,Guenther, Bettina,Hanreich, Reinhard
, p. 2288 - 2298 (2007/10/02)
The Synthesis and Hydrolysis of 6endo-Substituted 2endo-Norbornyl p-Toluenesulfonates; The hydrolysis products of the p-toluenesulfonates of several hitherto unknown 6endo-substituted 2endo-norbornanols have been determined.
Carbon Participation in the Solvolysis of 6-endo-substituted 2-exo-Norbornyl Toluenesulfonates. Norbornanes Part 6
Grob, Cyril A.,Guenther, Bettina,Hanreich, Reinhard
, p. 2312 - 2321 (2007/10/02)
The solvolysis rate constants k for the 6-endo-substituted 2-exo-norbornyl toluenesulfonates 7 have been determined.Values of logk correlate well with the respective inductive constants of the substituents 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.
