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Nuclear Magnetic Resonance Spectroscopy. Ring Inversion in 3,5,7-Cyclooctatrienone

Ganter, Camille and Pokras, Sanford M. and Roberts, John D. (1966) Nuclear Magnetic Resonance Spectroscopy. Ring Inversion in 3,5,7-Cyclooctatrienone. Journal of the American Chemical Society, 88 (18). pp. 4235-4237. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20151014-144942387

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Abstract

The rate of ring inversion in 3,5,7-cyclooctatrienone was determined by the temperature dependence of the nmr spectrum of the methylene protons adjacent to the carbonyl group. Inversion does not occur by rapid reversible formation of hydroxycyclooctatetraene because deuterium exchange of the methylene protons is much too slow for the operation of such a mechanism. It is suggested that a nearly planar transition state is involved. The activation energy for ring inversion was determined to be 11.9 ± 0.5 kcal/mole.


Item Type:Article
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http://dx.doi.org/10.1021/ja00970a023DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00970a023PublisherArticle
Additional Information:© 1966 American Chemical Society. Received March 31, 1966. Supported in part by the National Science Foundation; participant in the Undergraduate Research Program of the National Science Foundation.
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Caltech Gates and Crellin Laboratories of Chemistry3358
Issue or Number:18
Record Number:CaltechAUTHORS:20151014-144942387
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151014-144942387
Official Citation:Nuclear Magnetic Resonance Spectroscopy. Ring Inversion in 3,5,7-Cyclooctatrienone Camille Ganter, Sanford M. Pokras, and John D. Roberts Journal of the American Chemical Society 1966 88 (18), 4235-4237 DOI: 10.1021/ja00970a023
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61118
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:15 Oct 2015 17:07
Last Modified:03 Oct 2019 09:04

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