Roberts, John D. and Lee, C. C. and Saunders, W. H., Jr. (1955) Rearrangements in Carbonium Ion-Type Reactions of C^(14)-Labeled Dehydronorbornyl Derivatives. Journal of the American Chemical Society, 77 (11). pp. 3034-3037. ISSN 0002-7863. doi:10.1021/ja01616a034. https://resolver.caltech.edu/CaltechAUTHORS:20151021-142338708
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Abstract
Solvolysis of exo- and endo-dehydronorborn-C_2^(14) p-bromobenzenesulfonates in acetic acid and formic acid solutions and nitrous acid deaminations of endo-dehydronorbornyl-3-C^(14)-amine in acetic acid and aqueous fluoboric acid were found to yield 4-17% of dehydronorbornyl derivatives with 30-48% of the C^(14) located at other than the 2,3-positions. The C^(14) rearrangements are discussed in terms of unsymmetrical "dehydronorbornium" intermediates.
| Item Type: | Article | |||||||||
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| Additional Information: | © 1955 American Chemical Society. Received October 11, 1954. Supported in part by the joint program of the Office of Naval Research and the U. S. Atomic Energy Commission. Presented in part at the Symposium on Reaction Mechanisms at the 75th Anniversary Meeting of the American Chemical Society, September 7, 1951. | |||||||||
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| Issue or Number: | 11 | |||||||||
| DOI: | 10.1021/ja01616a034 | |||||||||
| Record Number: | CaltechAUTHORS:20151021-142338708 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20151021-142338708 | |||||||||
| Official Citation: | Rearrangements in Carbonium Ion-Type Reactions of C14-Labeled Dehydronorbornyl Derivatives John D. Roberts, C. C. Lee, and W. H. Saunders Jr. Journal of the American Chemical Society 1955 77 (11), 3034-3037 DOI: 10.1021/ja01616a034 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 61394 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Ruth Sustaita | |||||||||
| Deposited On: | 22 Oct 2015 18:25 | |||||||||
| Last Modified: | 10 Nov 2021 22:48 |
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