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

✍ Scribed by Helmut Duddeck

Publisher
John Wiley and Sons
Year
1975
Tongue
English
Weight
358 KB
Volume
7
Category
Article
ISSN
0749-1581

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✦ Synopsis

The chemical shifts of 4,, and 4eq substituted adamantanones are compared with those calculated with the aid of a given additivity rule. It is found that both 6 carbons are shielded with respect to the substituent. In contrast to the situation for the 71- atoms, however, the a ,,, atom is less shielded than the 6=,,,, 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 4,q substituted adamantanones. In both cases the measured values are 4 to 6ppm upfield. This can possibly be explained by an electronic interaction between the carbonyl group and the substituent.

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