Cox, Eugene F. and Caserio, Marjorie C. and Silver, Marc S. and Roberts, John D. (1961) Small-Ring Compounds. XXXIV. Carbonium Ion Reactions of 1-Methylcyclobutyl, (1-Methylcyclopropyl)-carbinyl and (β-Methylallyl)-carbinyl Derivatives. Journal of the American Chemical Society, 83 (12). pp. 2719-2724. ISSN 0002-7863. doi:10.1021/ja01473a028. https://resolver.caltech.edu/CaltechAUTHORS:20151020-083708026
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Abstract
(1-Methylcyclopropyl)-carbinyl chloride was found to solvolyze in 50% aqueous ethanol ca. ten times faster than 1-methylcyclobutyl chloride and as fast as t-butyl chloride. Treatment of (1-methylcyclopropyl)-carbinylamine and 1-methylcyclobutylamine with nitrous acid gave only 1-methylcyclobutanol. (β-Methylallyl)-carbinylamine gave the same alcohol as the only cyclic product. About 3% of the ^(14)C content of 1-methylcyclobutanol from the deamination of (1-methylcyclopropyl)-carbynil-α-^(14)C)-amine was found at the 3-position. These results are interpretable in terms of classical carbonium ions and/or substituted “bicyclobutonium” ion intermediates with fairly localized positive charges.
| Item Type: | Article | ||||||||||
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| Additional Information: | © 1961 American Chemical Society. Received December 30, 1960. Supported in part by the Petroleum Research Fund of the American Chemical Society and the U. S. Atomic Energy Commission. Grateful acknowledgment is hereby made to the Donors of said Fund. Presented at the Sixteenth National Organic Symposium of the American Chemical Society, Seattle, Wash., June, 1959. U. S. Rubber Co. Fellow, 1954-1955; National Science Foundation Predoctoral Fellow, 1955-1958. | ||||||||||
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| Issue or Number: | 12 | ||||||||||
| DOI: | 10.1021/ja01473a028 | ||||||||||
| Record Number: | CaltechAUTHORS:20151020-083708026 | ||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20151020-083708026 | ||||||||||
| Official Citation: | Small-Ring Compounds. XXXIV. Carbonium Ion Reactions of 1-Methylcyclobutyl, (1-Methylcyclopropyl)-carbinyl and (β-Methylallyl)-carbinyl Derivatives Eugene F. Cox, Marjorie C. Caserio, Marc S. Silver, and John D. Roberts Journal of the American Chemical Society 1961 83 (12), 2719-2724 DOI: 10.1021/ja01473a028 | ||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||
| ID Code: | 61309 | ||||||||||
| Collection: | CaltechAUTHORS | ||||||||||
| Deposited By: | Ruth Sustaita | ||||||||||
| Deposited On: | 20 Oct 2015 17:24 | ||||||||||
| Last Modified: | 10 Nov 2021 22:47 |
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