Definitive identification of the C-5 and C-7 NMR signals of adamantan-2-ol
β Scribed by S. Srivastava; C. K. Cheung; W. J. Le Noble
- Publisher
- John Wiley and Sons
- Year
- 1985
- Tongue
- English
- Weight
- 385 KB
- Volume
- 23
- Category
- Article
- ISSN
- 0749-1581
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β¦ Synopsis
The E and 2-5-deutenoadamant-2-ols have been synthesized by an unambiguous route. The =C NMR spectra show the familiar 1 : 1 : 1 splitting of one of the C-5 or C-7 signals, thus allowing a definite assignment of the &atoms to be made. This assignment is in accord with the conclusion of Duddeck and Islam. Revised assignments are offered for the reported configurations of the 5-bromo-and -chloro-adamantan-2-ols, and several unusual remote deuterium isotope shifts are reported.
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Comparison of a 'H coupled natural abundance "C NMR spectrum of l-oxo-1,2,3,4-tetrahydrocarbazole with a single-frequency experiment in which the hydrogens three bonds away from C-3 (indole numbering) were irradiated allowed the unambiguous distinction of the C-3 and C-3a signals. The results can be
## Abstract For Abstract see ChemInform Abstract in Full Text.
## Abstract Six groups of diastereomeric 2,4βdisubstituted adamantanes were studied with DFTβGIAOβNBO (natural orbital analysis) methods. The calculated ^13^C chemical shifts reproduce well the experimental data. It was found that among all diastereomers, those bearing substituents in Ξ΄β__syn__βaxi