Carbon-13 Nuclear Magnetic Resonance Spectroscopy. Conformational Analysis of Methyl-Substituted Cycloheptanes, Cycloheptanols, and Cycloheptanones
- Creators
- Christl, Manfred
- Roberts, John D.
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
- Eprint ID
- 60950
- Resolver ID
- CaltechAUTHORS:20151009-133524772
- NSF
- Max Kade Foundation, Inc.
- Created
-
2015-10-15Created from EPrint's datestamp field
- Updated
-
2021-11-10Created from EPrint's last_modified field
- Other Numbering System Name
- Caltech Gates and Crellin Laboratories of Chemistry
- Other Numbering System Identifier
- 4417