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Hetarynes. Part XV:N‐oxides of 2,3‐ and 3,4‐pyridyne

 

作者: R. J. Martens,   H. J. den Hertog,  

 

期刊: Recueil des Travaux Chimiques des Pays‐Bas  (WILEY Available online 1967)
卷期: Volume 86, issue 6  

页码: 655-669

 

ISSN:0165-0513

 

年代: 1967

 

DOI:10.1002/recl.19670860611

 

出版商: WILEY‐VCH Verlag

 

数据来源: WILEY

 

摘要:

AbstractThe action of potassium amide in liquid ammonia on theN‐oxides of 2‐, 3‐ and 4‐bromopyridine, 3‐fluoropyridine, 2‐ and 3‐bromo‐4‐methylpyridine, 3‐ and 4‐bromo‐5‐ethoxypyridine and 3‐ and 4‐bromo‐2,5‐dimethylpyridine has been investigated.3‐Fluoropyridine‐N‐oxide does not react under the conditions applied; the otherN‐oxides yield mixtures containing one or two amino compounds. The mechanisms of the formation of these substances are discussed.It was established that the SNAr2(= AE) reaction is almost the sole reaction pattern in the aminations of the 4‐bromopyridine‐N‐oxides and one of the mechanisms occurring in the aminations of the 2‐bromopyridine‐N‐oxides.The 2‐bromopyridine‐N‐oxides react partially and the 3‐bromopyridine‐N‐oxides exclusivelyvia2,3‐pyridyne‐N‐oxides as intermediates, except theN‐oxides of 3‐bromo‐2,5‐dimethylpyridine and 3‐br

 

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