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Rearrangement in the Reaction of Chlorobenzene-1-C^(14) with Potassium Amide

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. http://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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http://dx.doi.org/10.1021/ja01109a523DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01109a523PublisherArticle
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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Atomic Energy CommissionUNSPECIFIED
Record Number:CaltechAUTHORS:20151022-083819113
Persistent URL:http://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:22 Oct 2015 18:15

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