Westerman, Philip W. and Roberts, John D. (1977) ^(15)N Nuclear Magnetic Resonance Spectroscopy. Natural-Abundance ^(15)N Nuclear Magnetic Resonance Spectra of Enamines. Journal of Organic Chemistry, 42 (13). pp. 2249-2252. ISSN 0022-3263. doi:10.1021/jo00433a013. https://resolver.caltech.edu/CaltechAUTHORS:20151008-115810944
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Abstract
The ^(15)N chemical shifts of 18 cyclic enamines have been determined at the natural-abundance level of ^(15)N using the Fourier transform technique. The shifts depend on the size of both the cycloalkene and nitrogen-containing rings. Methyl substituents on the cycloalkene ring also influence the chemical shifts of enamines. Tertiary amines formed on hydrogenation of cyclic enamines are found to have ^(15)N chemical shifts 3.9-19.7 ppm upfield of the shift for the corresponding unsaturated compound. A carbonyl group in conjugation with an enamine group results in a large down field shift of approximately 30-40 ppm for the nitrogen resonance of the enamine.
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| Alternate Title: | Nitrogen-15 nuclear magnetic resonance spectroscopy. Natural abundance. Nitrogen-15 nuclear magnetic resonance spectra of enamines | |||||||||
| Additional Information: | © 1977 American Chemical Society. Received November 30, 1976. Supported by the Public Health Service, Research Grant GM-11072, from the Division of General Medical Sciences, and by the National Science Foundation. | |||||||||
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| Issue or Number: | 13 | |||||||||
| DOI: | 10.1021/jo00433a013 | |||||||||
| Record Number: | CaltechAUTHORS:20151008-115810944 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20151008-115810944 | |||||||||
| Official Citation: | Nitrogen-15 nuclear magnetic resonance spectroscopy. Natural abundance. Nitrogen-15 nuclear magnetic resonance spectra of enamines Philip W. Westerman and John D. Roberts The Journal of Organic Chemistry 1977 42 (13), 2249-2252 DOI: 10.1021/jo00433a013 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 60910 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Ruth Sustaita | |||||||||
| Deposited On: | 11 Oct 2015 11:20 | |||||||||
| Last Modified: | 10 Nov 2021 22:41 |
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