13C NMR spectral characterization of epimeric rotenone and some related tetrahydrobenzopyranofurobenzopyranones
Journal of Heterocyclic Chemistry
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By: S. L. Abidi and M.S. Abidi
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Abstract
The 13C nuclear magnetic resonance (nmr) spectra of epimers of rotenone and four 12a-hydroxy-analogues were examined to determine the stereochemical effect of the B/C ring fusion involving the 6a- and 12a-carbon centers. Chemical shift differences between the epimeric carbon resonances of cis- and trans-6a,12a-compounds were notably larger than those of diastereoisomers derived from the same B/C ring junction stereochemistry. Results of the spectral analysis have been useful for the quantification of mixtures of epimers and for the measurement of rates of epimerization and oxygenation.
| Publication type | Article |
|---|---|
| Publication Subtype | Journal Article |
| Title | 13C NMR spectral characterization of epimeric rotenone and some related tetrahydrobenzopyranofurobenzopyranones |
| Series title | Journal of Heterocyclic Chemistry |
| DOI | 10.1002/jhet.5570200649 |
| Volume | 20 |
| Issue | 6 |
| Year Published | 1983 |
| Language | English |
| Publisher | Wiley |
| Publisher location | Hoboken, NJ |
| Contributing office(s) | Upper Midwest Environmental Sciences Center |
| Description | 6 p. |
| Larger Work Type | Article |
| Larger Work Subtype | Journal Article |
| Larger Work Title | Journal of Heterocyclic Chemistry |
| First page | 1687 |
| Last page | 1692 |
| Google Analytic Metrics | Metrics page |