Published July 20, 1952
| public
Journal Article
Mechanisms of Acid Catalysis. The Kinetics and Mechanisms of the Acid-catalyzed Reactions of Ethyl Diazoacetate with Ethanol and Acetic Acid
- Creators
- Roberts, John D.
- Regan, Clare M.
- Allen, Inka
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.
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.Additional details
- Eprint ID
- 60664
- DOI
- 10.1021/ja01134a062
- Resolver ID
- CaltechAUTHORS:20151001-104312544
- Atomic Energy Commission
- Created
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2015-10-02Created from EPrint's datestamp field
- Updated
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2021-11-10Created from EPrint's last_modified field