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Carbon-13 Nuclear Magnetic Resonance Spectroscopy. Conformational Analysis of Methyl-Substituted Cycloheptanes, Cycloheptanols, and Cycloheptanones

Christl, Manfred and Roberts, John D. (1972) Carbon-13 Nuclear Magnetic Resonance Spectroscopy. Conformational Analysis of Methyl-Substituted Cycloheptanes, Cycloheptanols, and Cycloheptanones. Journal of Organic Chemistry, 37 (22). pp. 3443-3452. ISSN 0022-3263. http://resolver.caltech.edu/CaltechAUTHORS:20151009-133524772

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Abstract

The ^(13)C chemical shifts were determined of the carbons in 12 cycloheptanes, 21 cycloheptanols, and 8 cycloheptanones. In some cycloheptanols and cycloheptanones, the assignments have been obtained unambiguously by the synthesis of deuterated derivatives and the use of paramagnetic-shift reagents. Substituent effects for the different types of groups have been calculated. The most informative data about the cycloheptane conformations were provided by the relatively well understood y effects. The results are generally in good agreement with predictions based on the twist-chair form, which has been predicted by Hendrickson to be the most stable conformation. spectra. This fact was used to assign the resonances found for cis-trans mixtures of methyl-substituted cycloheptanols to specific isomers.


Item Type:Article
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http://dx.doi.org/10.1021/jo00795a014DOIArticle
http://pubs.acs.org/doi/abs/10.1021/jo00795a014PublisherArticle
Additional Information:© 1972 American Chemical Society. Received February 8, 1972. Supported by the National Science Foundation. Max Kade Foundation, Inc., Fellow, 1970-1971.
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Max Kade Foundation, Inc.UNSPECIFIED
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Caltech Gates and Crellin Laboratories of Chemistry4417
Record Number:CaltechAUTHORS:20151009-133524772
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151009-133524772
Official Citation:Carbon-13 nuclear magnetic resonance spectroscopy. Conformational analysis of methyl-substituted cycloheptanes, cycloheptanols, and cycloheptanones Manfred Christl and John D. Roberts The Journal of Organic Chemistry 1972 37 (22), 3443-3452 DOI: 10.1021/jo00795a014
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60950
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:15 Oct 2015 23:43
Last Modified:15 Oct 2015 23:43

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