Mazur, Robert H. and White, William N. and Semenow, Dorothy A. and Lee, C. C. and Silver, Marc S. and Roberts, John D. (1959) Small-ring Compounds. XXIII. The Nature of the Intermediates in Carbonium Ion-type Interconversion Reactions of Cyclopropylcarbinyl, Cyclobutyl and Allylcarbinyl Derivatives. Journal of the American Chemical Society, 81 (16). pp. 4390-4398. ISSN 0002-7863. doi:10.1021/ja01525a073. https://resolver.caltech.edu/CaltechAUTHORS:20151020-095615050
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Abstract
Investigation of the extent of isotope-position rearrangement in carbonium ion-type reactions of ^(14)C-labeled cyclopropylcarbinyl derivatives has revealed that the three methylene groups of the starting material achieve a striking degree of equivalence between reactants and products. These results, taken in conjunction with the abnormally large solvolytic reactivities of cyclopropylcarbinyl and cyclobutyl halides and sulfonate esters, can best be accounted for by assuming rapid but not instantaneous equilibration of three isomeric non-classical unsymmetrical “bicyclobutonium” ion intermediates.
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| Additional Information: | © 1959 American Chemical Society. Received September 4, 1958. 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 the Petroleum Research Fund. Presented in part at the 75th Anniversary Meeting of the American Chemical Society, September 7, 1951; National Research Council Postdoctoral Fellow, 1953-1954; National Science Foundation Predoctoral Fellow, 1955-1958. | ||||||||||
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| Issue or Number: | 16 | ||||||||||
| DOI: | 10.1021/ja01525a073 | ||||||||||
| Record Number: | CaltechAUTHORS:20151020-095615050 | ||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20151020-095615050 | ||||||||||
| Official Citation: | Small-ring Compounds. XXIII. The Nature of the Intermediates in Carbonium Ion-type Interconversion Reactions of Cyclopropylcarbinyl, Cyclobutyl and Allylcarbinyl Derivatives Robert H. Mazur, William N. White, Dorothy A. Semenow, C. C. Lee, Marc S. Silver, and John D. Roberts Journal of the American Chemical Society 1959 81 (16), 4390-4398 DOI: 10.1021/ja01525a073 | ||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||
| ID Code: | 61316 | ||||||||||
| Collection: | CaltechAUTHORS | ||||||||||
| Deposited By: | Ruth Sustaita | ||||||||||
| Deposited On: | 20 Oct 2015 18:23 | ||||||||||
| Last Modified: | 10 Nov 2021 22:47 |
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