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Ring inversion in 1,1-Dibenzylcyclohexanes

Levin, Ronald H. and Roberts, John D. and Kwart, H. and Walls, F. (1972) Ring inversion in 1,1-Dibenzylcyclohexanes. Journal of the American Chemical Society, 94 (19). pp. 6856-6857. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20151009-133525043

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Abstract

In a recent communication, the barrier to chair-chair interconversion in 1,1 -dimethyl-4,4-dibenzylcyclohexane (1a) was reported from studies of carbon and proton magnetic resonance spectroscopy to be at least 20 kcal/mol. This observation was surprising in terms of what is known about inversion barriers in cyclohexane and was rationalized in terms of hindered rotation of the benzyl groups.


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http://dx.doi.org/10.1021/ja00774a048DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00774a048PublisherArticle
Additional Information:© 1972 American Chemical Society. Received June 27, 1972. Supported by the National Science Foundation and the Public Health Service, Research Grant No. GM-11072 from the Division of General Medical Sciences. We are pleased to acknowledge helpful discussions with Professor G. Stork of Columbia University. National Institutes of Health Postdoctoral Fellow, 1971-1972.
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U.S. Public Health Service (USPHS)GM-11072
NIH Postdoctoral FellowshipUNSPECIFIED
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Caltech Gaies and Crellin Laboratories of Chemistry4448
Record Number:CaltechAUTHORS:20151009-133525043
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151009-133525043
Official Citation:Ring inversion in 1,1-dibenzylcyclohexanes Ronald H. Levin, John D. Roberts, H. Kwart, and F. Walls Journal of the American Chemical Society 1972 94 (19), 6856-6857 DOI: 10.1021/ja00774a048
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ID Code:60951
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:15 Oct 2015 22:27
Last Modified:15 Oct 2015 22:27

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