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The solvolyses of exo- and endo-5-norbornen-2-yl p-bromobenzenesulfonates. A re-investigation using deuterium nmr spectroscopy.

✍ Scribed by Jean-Marie Sonney; Pierre Vogel; Ulrich Burger

Publisher
Elsevier Science
Year
1978
Tongue
French
Weight
188 KB
Volume
19
Category
Article
ISSN
0040-4039

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✦ Synopsis

The solvolyses of 5-norbornen-2-yl esters have posed a considerable problem in interpretation, especially since there are divergences between the reported results. 1,2,3

Recently, It has been suggested on the basis of a tritium labeling study that the process involves a pair of enantiomeric homoallylic cations (1 and 2) equili--brating by Wagner-Meerwein and exo 3,2 hydride shifts which can further eliminate

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In the preceding letter we have reported on the apparently complex solvolyses of the norbornen-2-yl brosylates 1 and 2. In order to understand nore about the behaviour of hawallylic systems we have studied the acetolysis of the title cca-qzounds 2 and 4. In principle, both pair: of substrates (l/3 a