Renk, E. and Roberts, John D. (1961) Small-Ring Compounds. XXXII. The Reaction of Allylcarbinylamine-α-^(14)C (3-Butenyl-1-^(14)C-amine) with Nitrous Acid. Journal of the American Chemical Society, 83 (4). pp. 878-881. ISSN 0002-7863. doi:10.1021/ja01465a033. https://resolver.caltech.edu/CaltechAUTHORS:20151020-083706833
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Abstract
The isotopic analysis OF the cyclopropylcarbinol and cyclobutanol formed in the reaction of allycarbinylamine-α-^(14)C with nitrous acid has indicated that all of the possible methylene-labeled, isotope-position isomers are formed but not quite to the extent expected for statistical equilibrium. The compositions of the alcohols resulting from treatment of cyclopropylcarbinyl-,cyclobutyl- and allylcarbinylamines with nitrous acid have been measured accurately and correlated with the degree of isotope-position rearrangement obtained with ^(14)C-labeled amines. The results are in agreement with the previously postulated interpretation of these reactions as involving rapid but not instantaneous equilibration of unsymmetrical non-classical cations.
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| Additional Information: | © 1961 American Chemical Society. Received September 27, 1960. Supported in part by a grant from the Petroleum Research Fund of the American Chemical Society. Grateful acknowledgment is hereby made to the donors of this Fund. Presented at the Sixteenth National Organic Chemistry Symposium of the American Chemical Society, Seattle, Wash., June, 1959. | |||||||||
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| Issue or Number: | 4 | |||||||||
| DOI: | 10.1021/ja01465a033 | |||||||||
| Record Number: | CaltechAUTHORS:20151020-083706833 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20151020-083706833 | |||||||||
| Official Citation: | Small-Ring Compounds. XXXII. The Reaction of Allylcarbinylamine-α-14C (3-Butenyl-1-14C-amine) with Nitrous Acid E. Renk and John D. Roberts Journal of the American Chemical Society 1961 83 (4), 878-881 DOI: 10.1021/ja01465a033 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 61308 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Ruth Sustaita | |||||||||
| Deposited On: | 20 Oct 2015 17:17 | |||||||||
| Last Modified: | 10 Nov 2021 22:47 |
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