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The 1H NMR spectra of some norbornene derivatives, a LIS study

✍ Scribed by Raymond J. Abraham; Steven M. Coppell; Robert Ramage

Publisher
John Wiley and Sons
Year
1974
Tongue
English
Weight
418 KB
Volume
6
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The ^1^H NMR spectra of 2‐exo‐hydroxymethyl‐3‐endo‐methylnorbornene and the corresponding 2‐endo‐3‐exo isomer have been completely assigned with the aid of lanthanide reagents. This enabled a full analysis of the unusual spectrum of 2‐exo‐hydroxy‐methyl‐3‐endo‐methylnorbornene to be undertaken, confirming the proposed structure. The ΔEu values for 2‐exo‐hydroxymethyl‐3‐endo‐methylnorbornene and the 2‐endo‐3‐exo‐isomer have been used to test the effect of rotational averaging on the calculated pseudo contact shifts. Good agreement is obtained for a dynamic model in which the Eu atom exchanges between two sites on the oxygen atom of the OH bond, and in which the rotational equilibrium about the CHCH~2~OH bond is explicitly considered.

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