138826-33-2Relevant academic research and scientific papers
ON THE BIPYRIDYL FORMATION IN REACTIONS OF 2-CHLOROPYRIDINE DERIVATIVES WITH POTASSIUM AMIDE IN LIQUID AMMONIA
Streef, Johannis W.,Plas, Henk C. van der,Harkema, Sybolt
, p. 2313 - 2325 (2007/10/02)
In the reaction of 2,6-dichloropyridine and 2,6-dichloro-3-phenylpyridine with potassium amide in liquid ammonia at -70 deg 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 deg 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 deg C as well as -33 deg C, but in the presence of potassium permanganate at -33 deg 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.
