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^(15)N Nuclear Magnetic Resonance Spectroscopy. Natural-Abundance ^(15)N Nuclear Magnetic Resonance Spectra of Enamines

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. http://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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http://dx.doi.org/10.1021/jo00433a013DOIArticle
http://pubs.acs.org/doi/abs/10.1021/jo00433a013PublisherArticle
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.
Funders:
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U.S. Public Health Service (USPHS)GM-11072
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Caltech Gates and Crellin Laboratories of Chemistry5471
Record Number:CaltechAUTHORS:20151008-115810944
Persistent URL:http://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:11 Oct 2015 11:20

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