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Norbornanes. Part 20. Inductivity and bridging in 2-norbornyl cations

✍ Scribed by Rolf Bielmann; Francesco Fuso; Cyril A. Grob

Publisher: John Wiley and Sons
Year: 1988
Tongue: German
Weight: 447 KB
Volume: 71
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19880710203

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✦ Synopsis

As derived from the Hammetr equation log k/ko = pI 'cr ? where k and ko are rate constants for substituted and unsubstituted tosylates, respectively, and u? are inductive substituent constants [2]. The p , values for C(1) in 3 and 4 are presented and discussed in this communication. The dotted lines in 5 symbolize a weak bonding interaction.

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## Abstract A comparison of the solvolysis rates of the substituted 2‐__exo__‐ and 2‐__endo__ ‐norbornyl __p__‐toluenesulfonates **1, 2, 3** and **4** and the substituted 1‐ and 2‐adamantyl sulfonates **9** and **10**, respectively, in 80% ethanol and 97% trifluoroethanol has shown that the sensiti

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As measured by the pK, of 4-substituted quinuclidines [3] For the influence of 6-endo-substituents, see [2]. Derived from the equation log k = p,uy + log k,.

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## 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