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Nuclear Magnetic Resonance Spectroscopy. Conformational Equilibria and Equilibration of 4,4-Difluorocyclohexanone and 6,6-Difluoro-cis-decal-2-ones

Lack, Ruth E. and Ganter, Camille and Roberts, John D. (1968) Nuclear Magnetic Resonance Spectroscopy. Conformational Equilibria and Equilibration of 4,4-Difluorocyclohexanone and 6,6-Difluoro-cis-decal-2-ones. Journal of the American Chemical Society, 90 (25). pp. 7001-7007. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20151013-145415018

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Abstract

The rates of ring inversion and conformational equilibration of 6,6-difluoro-cis-decal-2-one and 10-methyl-6,6-difluoro-cis-decal-2-one have been determined using fluorine magnetic resonance spectroscopy. The activation energies were found to be 11.3 ± 0.3 and 9.5 ± 0.1 kcal/mol, respectively. 4,4-Difluorocyclohexanone, however, appears to exchange its fluorines between conformationally nonequivalent sites rapidly on the nmr time scale even at -180º.


Item Type:Article
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http://dx.doi.org/10.1021/ja01027a020DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01027a020PublisherArticle
Additional Information:© 1968 American Chemical Society. Received April 24, 1968. Supported in part by the National Science Foundation.
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Caltech Gates and Crellin Laboratories of Chemistry3653
Issue or Number:25
Record Number:CaltechAUTHORS:20151013-145415018
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151013-145415018
Official Citation:Nuclear magnetic resonance spectroscopy. Conformational equilibria and equilibration of 4,4-difluorocyclohexanone and 6,6-difluoro-cis-decal-2-ones Ruth E. Lack, Camille Ganter, and John D. Roberts Journal of the American Chemical Society 1968 90 (25), 7001-7007 DOI: 10.1021/ja01027a020
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61082
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:14 Oct 2015 19:36
Last Modified:03 Oct 2019 09:04

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