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The Mechanism of Aminations of Halobenzenes

Roberts, John D. and Semenow, Dorothy A. and Simmons, Howard E., Jr. and Carlsmith, L. A. (1956) The Mechanism of Aminations of Halobenzenes. Journal of the American Chemical Society, 78 (3). pp. 601-611. ISSN 0002-7863. doi:10.1021/ja01584a024.

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An elimination-addition mechanism, probably involving a "benzyne" intermediate, has been established for the rearrangements which often occur in the conversion of non-activated aryl halides to arylamines with metallic amides. The evidence for the "benzyne" intermediate was obtained through ^(14)C-tracer studies of rearrangements with halobenzenes and experiments designed to determine the role of the hydrogen atom located ortho to the displaced halogen atom.

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Additional Information:© 1956 American Chemical Society. Received August 22, 1955. Supported in part by the program of research of the U. S. Atomic Energy Commission. Presented in part at the Kansas City Meeting of the American Chemical Society, March 24, 1954. Skinner Fellow of Mt. Holyoke College, 1953-1954; National Science Foundation Predoctoral Fellow, 1954-1955.
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Atomic Energy CommissionUNSPECIFIED
Mt. Holyoke CollegeUNSPECIFIED
NSF Predoctoral FellowshipUNSPECIFIED
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Caltech Gates and Crellin Laboratories of Chemistry2028
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Official Citation:The Mechanism of Aminations of Halobenzenes John D. Roberts, Dorothy A. Semenow, Howard E. Simmons Jr., and L. A. Carlsmith Journal of the American Chemical Society 1956 78 (3), 601-611 DOI: 10.1021/ja01584a024
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61381
Deposited By: Ruth Sustaita
Deposited On:22 Oct 2015 02:01
Last Modified:10 Nov 2021 22:48

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