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Exchange Reactions of Deuterated Benzene Derivatives with Potassium Amide in Liquid Ammonia

Hall, George E. and Piccolini, Richard and Roberts, John D. (1955) Exchange Reactions of Deuterated Benzene Derivatives with Potassium Amide in Liquid Ammonia. Journal of the American Chemical Society, 77 (17). pp. 4540-4543. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20151021-125953236

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Abstract

The rates of deuterium-protium exchange have been determined for o-, m- and p-deuterated fluorobenzene, benzotri-fluoride and anisole in liquid ammonia solution in the presence of potassium amide. The exchange rates were found to be greatest for the ortho compounds and smallest for the para compounds. Deuterobenzene and o-deuterotoluene reacted too slowly for convenient measurement. The results are interpreted on the basis of the operation of combined inductive and field effects of the substituents, mesomeric effects appearing to be of minor importance.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja01622a033DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01622a033PublisherArticle
Additional Information:© 1955 American Chemical Society. Received March 7, 1955. Supported in part by The Upjohn Company. Faculty Fellow of The Fund for the Advancement of Education, 1953-1954.
Funders:
Funding AgencyGrant Number
Upjohn CompanyUNSPECIFIED
Advancement of Education FundUNSPECIFIED
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Other Numbering System NameOther Numbering System ID
Caltech Gates and Crellin Laboratories of Chemistry1977
Record Number:CaltechAUTHORS:20151021-125953236
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151021-125953236
Official Citation:Exchange Reactions of Deuterated Benzene Derivatives with Potassium Amide in Liquid Ammonia George E. Hall, Richard Piccolini, and John D. Roberts Journal of the American Chemical Society 1955 77 (17), 4540-4543 DOI: 10.1021/ja01622a033
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61383
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:21 Oct 2015 22:47
Last Modified:21 Oct 2015 22:47

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