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The Reaction of Ethylamine-1-C^(14) with Nitrous Acid

Roberts, John D. and Yancey, Joel A. (1952) The Reaction of Ethylamine-1-C^(14) with Nitrous Acid. Journal of the American Chemical Society, 74 (23). pp. 5943-5945. ISSN 0002-7863. doi:10.1021/ja01143a037.

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Ethylamine-1-C^(14) on treatment with perchloric acid and sodium nitrite in aqueous solution gave ethylene and a 38% yield of C^(l4)-labeled ethanol which was shown by degradation and C^(14)-analysis to contain 1.5% of the rearrangement product, ethanol-2-C^(l4). The rearrangement product was demonstrated not to be formed in the degradation procedure or by hydration of the ethylene produced in the amine-nitrous acid reaction. It is concluded that the ethyl cation is not converted to ethyleneprotonium ion (II) at a rate which is comparable to that of its reaction with water. The reaction of ethylamine with perchloric acid and sodium nitrite in 99.8% deuterium oxide gave ethanol which contained only 1.1 atom % of deuterium attached to carbon. This result indicates that less than 10% of the ethanol could have been formed via diazoethane as an intermediate.

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Additional Information:© 1952 American Chemical Society. Received July 18, 1952. Supported in part by the program of research of the Office of Naval Research and the U. S. Atomic Energy Commission. Presented at the Symposium on Reaction Mechanisms at the 75th Anniversary Meeting of the American Chemical Society, September 7, 1951.
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Office of Naval Research (ONR)UNSPECIFIED
Atomic Energy CommissionUNSPECIFIED
Issue or Number:23
Record Number:CaltechAUTHORS:20151022-111328435
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Official Citation:The Reaction of Ethylamine-1-C14 with Nitrous Acid John D. Roberts and Joel A. Yancey Journal of the American Chemical Society 1952 74 (23), 5943-5945 DOI: 10.1021/ja01143a037
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61415
Deposited By: Ruth Sustaita
Deposited On:22 Oct 2015 22:13
Last Modified:10 Nov 2021 22:48

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