Silver, Marc S. and Caserio, Marjorie C. and Rice, Howard E. and Roberts, John D. (1961) Small-Ring Compounds. XXXV. Studies of Rearrangements in the Nitrous Acid Deaminations of Methyl-substituted Cyclobutyl-, Cyclopropylcarbinyl- and Allylcarbinylamines. Journal of the American Chemical Society, 83 (17). pp. 3671-3678. ISSN 0002-7863. doi:10.1021/ja01478a028. https://resolver.caltech.edu/CaltechAUTHORS:20151020-083706149
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Abstract
The compositions of the alcohol mixtures formed in nitrous acid deaminations of cyclopropylmethylcarbinylamine, (2-methylcyclopropyl)-carbinylamine, 2-methylcyclobutylamine, 3-methylcyclobutylamine, crotylcarbinylamine and allylmethylcarbinylamine have been determined. These results and the behavior of the corresponding alcohols under isomerization conditions in strongly acidic media may be explained by assuming formation of three non-equivalent, unsymmetrical, non-classical cationic intermediates analogous to those previously proposed for the carbonium ion reactions of other small ring derivatives.
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| Additional Information: | © 1961 American Chemical Society. Received March 3, 1961. Supported in part by the National Science Foundation and 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, June 15, 1959, Seattle, Wash.; of the Symposium Abstracts, p. 1-10. National Science Foundation Predoctoral Fellow, 1955-1958. | |||||||||
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| Issue or Number: | 17 | |||||||||
| DOI: | 10.1021/ja01478a028 | |||||||||
| Record Number: | CaltechAUTHORS:20151020-083706149 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20151020-083706149 | |||||||||
| Official Citation: | Small-Ring Compounds. XXXV. Studies of Rearrangements in the Nitrous Acid Deaminations of Methyl-substituted Cyclobutyl-, Cyclopropylcarbinyl- and Allylcarbinylamines Marc S. Silver, Marjorie C. Caserio, Howard E. Rice, and John D. Roberts Journal of the American Chemical Society 1961 83 (17), 3671-3678 DOI: 10.1021/ja01478a028 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 61307 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Ruth Sustaita | |||||||||
| Deposited On: | 20 Oct 2015 17:15 | |||||||||
| Last Modified: | 10 Nov 2021 22:47 |
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