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Rearrangements in Carbonium-ion Type Reactions of C^(14)-Labeled Pentamethylethanol (2,3,3-Trimethyl-2-butanol-1-C^(14))

Roberts, John D. and Yancey, Joel A. (1955) Rearrangements in Carbonium-ion Type Reactions of C^(14)-Labeled Pentamethylethanol (2,3,3-Trimethyl-2-butanol-1-C^(14)). Journal of the American Chemical Society, 77 (21). pp. 5558-5562. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20151021-125953572

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Abstract

Treatment of 2,3,3-trimethyl-2-butanol-1-C^(14) with concentrated hydrochloric acid and zinc chloride (Lucas reagent) yielded 2-chloro-2,3,3-trimethylbutane with the C^(14) distributed essentially equally among the five methyl groups. Under the conditions used, the aliphatic chloride equilibrated completely with Lucas reagent containing radioactive chloride ion. The rearrangement and chloride exchange may be accounted for by the following equilibria involving solvated carbonium ions.


Item Type:Article
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URLURL TypeDescription
http://dx.doi.org/10.1021/ja01626a036DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01626a036PublisherArticle
Additional Information:© 1955 American Chemical Society. Received May 9, 1955. Supported in part by the joint program of research of the Office of Naval Research and the U. S. Atomic Energy Commission. Presented at the Symposium on Reaction Mechanisms at the 75th Anniversary of the American Chemical Society, September 13, 1951.
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Office of Naval Research (ONR)UNSPECIFIED
Atomic Energy CommissionUNSPECIFIED
Issue or Number:21
Record Number:CaltechAUTHORS:20151021-125953572
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151021-125953572
Official Citation:Rearrangements in Carbonium-ion Type Reactions of C14-Labeled Pentamethylethanol (2,3,3-Trimethyl-2-butanol-1-C14) John D. Roberts and Joel A. Yancey Journal of the American Chemical Society 1955 77 (21), 5558-5562 DOI: 10.1021/ja01626a036
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61384
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:22 Oct 2015 01:36
Last Modified:03 Oct 2019 09:07

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