Roberts, John D. and Yancey, Joel A. (1953) Mechanisms of Racemization of Camphene-8-C^(14). Journal of the American Chemical Society, 75 (13). pp. 3165-3168. ISSN 0002-7863. doi:10.1021/ja01109a037. https://resolver.caltech.edu/CaltechAUTHORS:20151022-111327424
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Abstract
It has been shown by C^(14)-tracer studies that optically-active camphene racemizes by at least two different mechanisms in the presence of hydrated titanium dioxide, pyruvic acid or aniline hydrochloride. One of these mechanisms does not cause isotope-position rearrangement of camphene-8-C^(14) and probably involves successive hydride and Wagner rearrangements. This mechanism predominates with hydrated titanium dioxide and aniline hydrochloride. Racemization of camphene-8-C^(14) with pyruvic acid is accompanied by extensive isotope-position rearrangement and is-well formulated by assuming interconversion of enantiomorphic "camphenonium" (camphene-hydro) cations through methyl group shifts (Nametkin rearrangements).
| Item Type: | Article | |||||||||
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| Additional Information: | © 1953 American Chemical Society. Received January 3, 1953. Supported in part by the program of research of the U. S. Atomic Energy Commission. | |||||||||
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| Issue or Number: | 13 | |||||||||
| DOI: | 10.1021/ja01109a037 | |||||||||
| Record Number: | CaltechAUTHORS:20151022-111327424 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20151022-111327424 | |||||||||
| Official Citation: | Mechanisms of Racemization of Camphene-8-C14 John D. Roberts and Joel A. Yancey Journal of the American Chemical Society 1953 75 (13), 3165-3168 DOI: 10.1021/ja01109a037 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 61412 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Ruth Sustaita | |||||||||
| Deposited On: | 22 Oct 2015 18:44 | |||||||||
| Last Modified: | 10 Nov 2021 22:48 |
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