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Nuclear Magnetic Resonance Spectroscopy. Conformational Equilibration of Cycloheptane and Cycloheptene Derivatives

Glazer, Edward S. and Knorr, Rudolf and Ganter, Camille and Roberts, John D. (1972) Nuclear Magnetic Resonance Spectroscopy. Conformational Equilibration of Cycloheptane and Cycloheptene Derivatives. Journal of the American Chemical Society, 94 (17). pp. 6026-6032. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20151009-133525322

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Abstract

A study of the temperature dependence of the ^(19)F nuclear magnetic resonance (nmr) spectra of 4,4-difluoro-1,1-dimethylcycloheptane has shown that, at low temperatures, this substance exists predominantly in the twist-chair conformation with the methyl groups on the axis carbon atom. 1 ,1-Difluoro-4,5-trans-dibromocycloheptane, at low temperatures, exists predominantly in two different Conformations with the fluorine atoms at the axis carbon atom. 5,5-Difluorocycloheptene, at low temperatures, exists in a single conformation best represented as the chair. Activation parameters have been obtained for the conformational equilibration of these derivatives. For 1,1- difluorocycloheptane, 1,1,3,3-tetrafluorocycloheptane, and 4,4-difluoro-1-tert-butylcycloheptane the conformational equilibria are still rapid on the nmr time scale at low temperatures and only qualitative conclusions can be drawn about their conformations.


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http://dx.doi.org/10.1021/ja00772a015DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00772a015PublisherArticle
Additional Information:© 1972 American Chemical Society. Received October 16, 1971. Work supported by the National Science Foundation. Presented in part at the 19th National Organic Chemistry Symposium of the American Chemical Society, Tempe, Arizona, June 17, 1965.
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Caltech Gates and Crellin Laboratories of Chemistry4359
Record Number:CaltechAUTHORS:20151009-133525322
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151009-133525322
Official Citation:Nuclear magnetic resonance spectroscopy. Conformational equilibration of cycloheptane and cycloheptene derivatives Edward S. Glazer, Rudolf Knorr, Camille Ganter, and John D. Roberts Journal of the American Chemical Society 1972 94 (17), 6026-6032 DOI: 10.1021/ja00772a015
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60952
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:16 Oct 2015 17:56
Last Modified:16 Oct 2015 17:56

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