Carbon‐13 nuclear magnetic resonance spectra. I—Monosubstituted adamantanes and adamantanones

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Abstract
The chemical shifts of 4ax and 4eq substituted adamantanones are compared with those calculated with the aid of a given additivity rule. It is found that both δ carbons are shielded with respect to the substituent. In contract to the situation for the y‐atoms, however, the δsyn atom is less shielded than the δanti atom. In most cases the additivity rule predicts the chemical shifts with an accuracy of approximately 1 ppm. Exceptions are carbon atoms 4 and 9 of the 4eq substituted adamantanones. In both cases the measured values are 4 to 6 ppm upfield. This can possibly be explained by an electronic interaction between the carbonyl group and the substituent.

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