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Rearrangements in the Reactions of 2-(4-Substituted)-phenylethylamines-1-C^(14) with Nitrous Acid

Roberts, John D. and Regan, Clare M. (1953) Rearrangements in the Reactions of 2-(4-Substituted)-phenylethylamines-1-C^(14) with Nitrous Acid. Journal of the American Chemical Society, 75 (9). pp. 2069-2072. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20151022-111328142

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Abstract

Treatment of a series of C^(14)-labeled 2-(4-substituted)-phenylethylamines (X-CH_2C^(14)H_2NH_2) with nitrous acid in water and acetic acid has been found to yield more or less of the isotope-position rearrangement products (X-C^(14)H_2CH_2Y; Y = -OH or -0Ac) depending on the solvent and the nature of X. With X = -OCH_8, -H and -NO_2, the most rearrangement (45%) was observed in acetic acid with X = -OCH_8, and the least (~5%) rearrangement when X = -NO_2 in water or acetic acid.


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http://dx.doi.org/10.1021/ja01105a014DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01105a014PublisherArticle
Additional Information:© 1953 American Chemical Society. Received September 29, 1952. Presented in part at the Symposium on Reaction Mechanisms at the 75th Anniversary Meeting of the American Chemical Society, September 7, 1951. Supported in part by the program of research of the U. S. Atomic Energy Commission.
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Record Number:CaltechAUTHORS:20151022-111328142
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20151022-111328142
Official Citation:Rearrangements in the Reactions of 2-(4-Substituted)-phenylethylamines-1-C14 with Nitrous Acid John D. Roberts and Clare M. Regan Journal of the American Chemical Society 1953 75 (9), 2069-2072 DOI: 10.1021/ja01105a014
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61414
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:22 Oct 2015 22:11
Last Modified:22 Oct 2015 22:11

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