Helvetica Chimica Acta p. 2443 - 2447 (1982)
Update date:2022-08-17
Topics:
Grob, Cyril A.
Herzfeld, Danielle
The solvolysis products of the stereoisomeric 6-cyano-2-norbornyl p-toluenesulfonates 1-4 (R = CN) in dioxane/water 7 : 3 have been determined.In contrast to an earlier report the 6exo-cyano-2exo-norbornyl p-toluenesulfonate (1; R = CN) yields 30percent of the 2endo-alcohol 9 (R = CN) beside the 2exo-alcohol 10 and the norbornenes 12 and 13.The results confirm that -I substituents at C(6) reduce 1,3-bridging in the intermediate norbornyl cation and hence its rate of rearrangement.The relatively high rate constants for some 6-fluoro- and 6-cyano-2exo-norbornyl p-toluenesulfonates are ascribed to C,C-hyperconjugation assisted by the conjugative effects of the 6-fluoro and cyano substituents.
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