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Mechanisms of Racemization of Camphene-8-C^(14)

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. http://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).


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http://dx.doi.org/10.1021/ja01109a037DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01109a037PublisherArticle
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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Atomic Energy CommissionUNSPECIFIED
Record Number:CaltechAUTHORS:20151022-111327424
Persistent URL:http://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:22 Oct 2015 18:44

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