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Published November 1, 1972 | public
Journal Article

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

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.

Additional Information

© 1972 American Chemical Society. Received February 8, 1972. Supported by the National Science Foundation. Max Kade Foundation, Inc., Fellow, 1970-1971.

Additional details

Created:
August 19, 2023
Modified:
October 24, 2023