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Intermediates in the Nitrous Acid Deamination of 2-[p-(2'-Hydroxyethoxy)phenyl]ethylamine

Caserio, Marjorie C. and Levin, Robert D. and Roberts, John D. (1965) Intermediates in the Nitrous Acid Deamination of 2-[p-(2'-Hydroxyethoxy)phenyl]ethylamine. Journal of the American Chemical Society, 87 (24). pp. 5651-5655. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20151015-104927388

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Abstract

Nitrous acid deamination in water and in acetic acid of the para-substituted 2-phenylethylamine, p-HOCH_2-CH_2OC_6H_4CH_2CH_2NH_2 and the corresponding deuterated amine p-HOCD_2CH_2OC_6H_4CH_2CD_2NH_2, resulted in 39-40 % isotope-position migration in the ethyl group as determined from the nuclear magnetic resonance spectra of the products obtained from the deuterated amine. Aryl migration between the oxygens of the hydroxyethoxy group was considered possible but was not observed.


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http://dx.doi.org/10.1021/ja00952a024DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja00952a024PublisherArticle
Additional Information:© 1965 American Chemical Society. Received July 6, 1965. 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 Chemistry3274
Issue or Number:24
Record Number:CaltechAUTHORS:20151015-104927388
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151015-104927388
Official Citation:Intermediates in the Nitrous Acid Deamination of 2-[p-(2'-Hydroxyethoxy)phenyl]ethylamine Marjorie C. Caserio, Robert D. Levin, and John D. Roberts Journal of the American Chemical Society 1965 87 (24), 5651-5655 DOI: 10.1021/ja00952a024
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61161
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:16 Oct 2015 19:01
Last Modified:03 Oct 2019 09:04

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