On the bipyridyl formation in reactions of 2-chloropyridine derivatives with potassium amide in liquid ammonia

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Title:On the bipyridyl formation in reactions of 2-chloropyridine derivatives with potassium amide in liquid ammonia
Creators:
Streef, Johannis W.
van der Plas, Henk C.
Harkema, Sybolt
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 56, 11, pp. 2313-2325

Abstract

In the reaction of 2,6-dichloropyridine and 2,6-dichloro-3-phenylpyridine with potassium amide in liquid ammonia at –70°C, formation of derivatives of 4,4’-bipyridyl and 3,4’-bipyridyl is observed. The 4,4’ coupling products are far in excess to the 3,4’ coupling products. When the reaction is carried out at –70°C in the presence of potassium permanganate, the corresponding 4-aminopyridines are the main products. 2-Chloro-6-phenoxypyridine is very unreactive with this aminating reagent at –70°C as well as –33°C, but in the presence of potassium permanganate at –33°C 4-amino-2-chloro-6-phenoxypyridine is formed in fair yield. The mechanisms of the formation of the bipyridyls and 4-aminopyridines are presented.

Title:On the bipyridyl formation in reactions of 2-chloropyridine derivatives with potassium amide in liquid ammonia
Creators:
Streef, Johannis W.
van der Plas, Henk C.
Harkema, Sybolt
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:56
Number:11
Page Range:pp. 2313-2325
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19912313UNSPECIFIED
ID Code:5161
Item Type:Article
Deposited On:22 Feb 2010 11:32
Last Modified:22 Feb 2010 10:32

Citation

Streef, Johannis W.; van der Plas, Henk C.; Harkema, Sybolt (1991) On the bipyridyl formation in reactions of 2-chloropyridine derivatives with potassium amide in liquid ammonia. Collection of Czechoslovak Chemical Communications, 56 (11). pp. 2313-2325. ISSN 0010-0765

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