Roberts, John D. and Simmons, Howard E., Jr. and Carlsmith, L. A. and Vaughan, C. Wheaton (1953) Rearrangement in the Reaction of Chlorobenzene-1-C^(14) with Potassium Amide. Journal of the American Chemical Society, 75 (13). pp. 3290-3291. ISSN 0002-7863. doi:10.1021/ja01109a523. https://resolver.caltech.edu/CaltechAUTHORS:20151022-083819113
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Abstract
No satisfactory explanation has been published for the rearrangements which often occur in the amination of “non-activated” aryl halides with alkalimetal amides. The pattern of the rearrangements shows a considerable disregard for the influences governing the usual aromatic substitutions and is well illustrated by the products obtained from the amination of the methoxy- and trifluoromethylhalobenzenes. Although the methoxy- and trifluoromethyl groups orient oppositely in aromatic nitration, o- and m-methoxy- and trihoromethylhalobenzenes with alkali-metal amides yield exclusively m-substituted anilines, while the p-isomers yield mixtures containing roughly equal amounts of m- and p-substituted aniline.
| Item Type: | Article | |||||||||
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| Additional Information: | © 1953 American Chemical Society. Received March 12, 1953. Supported in part by the program of research of the U. S. Atomic Energy Commission. | |||||||||
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| Issue or Number: | 13 | |||||||||
| DOI: | 10.1021/ja01109a523 | |||||||||
| Record Number: | CaltechAUTHORS:20151022-083819113 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20151022-083819113 | |||||||||
| Official Citation: | REARRANGEMENT IN THE REACTION OF CHLOROBENZENE-1-C14 WITH POTASSIUM AMIDE John D. Roberts, Howard E. Simmons Jr., L. A. Carlsmith, and C. Wheaton Vaughan Journal of the American Chemical Society 1953 75 (13), 3290-3291 DOI: 10.1021/ja01109a523 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 61409 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Ruth Sustaita | |||||||||
| Deposited On: | 22 Oct 2015 18:15 | |||||||||
| Last Modified: | 10 Nov 2021 22:48 |
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