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. doi:10.1016/0040-4020(58)80015-0. 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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| 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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| Issue or Number: | 3 | |||||||||
| DOI: | 10.1016/0040-4020(58)80015-0 | |||||||||
| 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) | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 61531 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Ruth Sustaita | |||||||||
| Deposited On: | 27 Oct 2015 16:14 | |||||||||
| Last Modified: | 10 Nov 2021 22:50 |
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