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Carbon-13 chemical shifts of bicyclo[3.2.1]octane and bicyclo[2.2.1]heptane derivatives

✍ Scribed by E. Lippmaa; T. Pehk; N. A. Belikova; A. A. Bobyleva; A. N. Kalinichenko; M. D. Ordubadi; A. F. Platé

Publisher
John Wiley and Sons
Year
1976
Tongue
English
Weight
582 KB
Volume
8
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

^13^C chemical shifts of more than fifty bicyclo[3.2.1]octane and bicyclo[2.2.1]heptane derivatives (hydrocarbons, alcohols, ketones and esters) have been determined. The usefulness of ethyl derivatives for the assignment of close ^13^C chemical shifts in bicyclic methyl derivatives is shown both for the bicyclo[3.2.1]octane and bicyclo[2.2.1]heptane series. Comparison of substituent effects on α‐, β‐, γ‐ and δ‐carbons in both series of compounds shows remarkable differences in steric interactions. In contrast to the rigid bicyclo[2.2.1]heptane system, both chair and boat conformations can be predominant in the bicyclo[3.2.1]octane series with the conformationally flexible 6‐membered ring.

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The 'H and I3C NMR spectra of six bromo-and methoxybicyclo[3.2.1]octanes were completely assigned. An axial bromine substituent at C-2 or C-4 results in a 5 ppm upfield shift of C-8 due to the gauche interaction. An equatorial bromine results in an upfield shift of similar magnitude on either C-6 (o