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HYDROGEN ISOTOPE EFFECT IN THE AMINATION OF CHLOROBENZENE BY SODAMIDE

 

作者: G. E. Dunn,   Peter J. Krueger,   Walter Rodewald,  

 

期刊: Canadian Journal of Chemistry  (NRC Available online 1961)
卷期: Volume 39, issue 1  

页码: 180-191

 

ISSN:0008-4042

 

年代: 1961

 

DOI:10.1139/v61-022

 

出版商: NRC Research Press

 

数据来源: NRC

 

摘要:

Mixtures of chlorobenzene and chlorobenzene-2-2H have been subjected to partial amination by sodamide in liquid ammonia and both the unreacted starting material and the product aniline have been analyzed for deuterium. Deuterium in the aniline is distributed approximately equally between the ortho and meta positions. The results give strong support to the mechanism proposed by Roberts and co-workers in which the slow step is the formation of an intermediate, such as benzyne, which is symmetrical with respect to carbon atoms 1 and 2.

 

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