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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. doi:10.1021/ja01109a037.

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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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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
Issue or Number:13
Record Number:CaltechAUTHORS:20151022-111327424
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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
Deposited By: Ruth Sustaita
Deposited On:22 Oct 2015 18:44
Last Modified:10 Nov 2021 22:48

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