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Mechanisms of Acid Catalysis. The Kinetics and Mechanisms of the Acid-catalyzed Reactions of Ethyl Diazoacetate with Ethanol and Acetic Acid

Roberts, John D. and Regan, Clare M. and Allen, Inka (1952) Mechanisms of Acid Catalysis. The Kinetics and Mechanisms of the Acid-catalyzed Reactions of Ethyl Diazoacetate with Ethanol and Acetic Acid. Journal of the American Chemical Society, 74 (14). pp. 3679-3683. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20151001-104312544

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Abstract

The p-toluenesulfonic acid-catalyzed reaction of ethyl diazoacetate with ethanol has been found to have different hydrogen isotope and solvent effects from the formally similar reaction with diphenyldiazomethane. Deuterium-exchange experiments have demonstrated that ethyl diazoacetate is involved in a rapid and reversible equilibrium with the corresponding diazonium ion with p-toluenesulfonic acid in ethanol, in the absence of strong acid in acetic acid or with acetic acid in benzene. It is concluded that the general-acid and “specific-oxonium” catalyzed reactions of diazo compounds involve different types of mechanisms.


Item Type:Article
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URLURL TypeDescription
http://dx.doi.org/10.1021/ja01134a062DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01134a062PublisherArticle
Additional Information:© 1952 American Chemical Society. We are indebted to Mr. David B. Kellom for the deuterium analyses reported in Table III. Supported in part by the program of research of the United States Atomic Energy Commission.
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Atomic Energy CommissionUNSPECIFIED
Issue or Number:14
Record Number:CaltechAUTHORS:20151001-104312544
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151001-104312544
Official Citation:Mechanisms of Acid Catalysis. The Kinetics and Mechanisms of the Acid-catalyzed Reactions of Ethyl Diazoacetate with Ethanol and Acetic Acid John D. Roberts, Clare M. Regan, and Inka Allen Journal of the American Chemical Society 1952 74 (14), 3679-3683 DOI: 10.1021/ja01134a062
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60664
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:02 Oct 2015 16:34
Last Modified:03 Oct 2019 08:59

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