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Reactions of non-activated aryl halides with nucleophilic agents induced by alkali amides in liquid ammonia

Scardiglia, Franco and Roberts, John D. (1958) Reactions of non-activated aryl halides with nucleophilic agents induced by alkali amides in liquid ammonia. Tetrahedron, 3 (3). pp. 197-208. ISSN 0040-4020. https://resolver.caltech.edu/CaltechAUTHORS:20151026-152654071

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Abstract

It has been shown that the reactions of nucleophiles with non-activated aryl halides, discovered by Bergstrom to be induced by alkali amides in liquid ammonia, proceed by way of a benzyne-type intermediate. The ease with which a given nucleophile can compete with amide ion does not appear to be a simple function of either its basic strength or nucleophilic character as measured in other reactions. Thus, the anions of a number of weak acids line up qualitatively in competitive power as follows: fluorenyl anion ~ anilide > thiophenolate ~ triphenylmethide > acetophenone enolate anion ~ phenylacetylide > phenolate > pyrrolate > alkoxides, iodide or cynaide. The results indicate benzyne to be a highly unstable entity.


Item Type:Article
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http://dx.doi.org/10.1016/0040-4020(58)80015-0DOIArticle
http://www.sciencedirect.com/science/article/pii/0040402058800150PublisherArticle
Additional Information:© Pergamon Press Ltd. Received 21 November 1957. Supported in part by the Petroleum Research Fund administered by the American Chemical Society. Grateful acknowledgement is hereby made to the Donors of said Fund. Gates and Crellin Laboratories of Chemistry, California Institute of Technology, Pasadena, Calif. Contribution No. 2241, Gates and Crellin Laboratories of Chemistry, California Institute of Technology, Pasadena, California. USA.
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American Chemical Society Petroleum Research FundUNSPECIFIED
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Caltech Gates and Crellin Laboratories of Chemistry2241
Issue or Number:3
Record Number:CaltechAUTHORS:20151026-152654071
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151026-152654071
Official Citation:Franco Scardiglia, John D. Roberts, Reactions of non-activated aryl halides with nucleophilic agents induced by alkali amides in liquid ammonia, Tetrahedron, Volume 3, Issue 3, 1958, Pages 197-208, ISSN 0040-4020, http://dx.doi.org/10.1016/0040-4020(58)80015-0. (http://www.sciencedirect.com/science/article/pii/0040402058800150)
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ID Code:61531
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:27 Oct 2015 16:14
Last Modified:03 Oct 2019 09:09

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