Premium
Diazotization–cyanation of aromatic amines with crosslinked poly(4‐vinylpyridine)‐supported cyanide ions
Author(s) -
Karimi Zarchi Mohammad Ali,
Ebrahimi Nahid
Publication year - 2012
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.36394
Subject(s) - cyanation , chemistry , nitrile , sulfuric acid , cyanide , reagent , tetrafluoroborate , aryl , acetonitrile , yield (engineering) , polymer chemistry , amine gas treating , inorganic chemistry , polymer , nuclear chemistry , organic chemistry , materials science , catalysis , alkyl , ionic liquid , metallurgy
A simple, mild, and efficient method for the cyanation of stable arenediazonium salts was developed with polymer‐supported cyanide. Arenediazonium hydrogen sulfate (ArN 2 + HSO 4 − ) was obtained by the reaction between a primary aryl amine and sodium nitrite in the presence of concentrated sulfuric acid (H 2 SO 4 ) at low temperature (0–5°C). By an ion‐exchange reaction between ArN 2 + HSO 4 − and NaBF 4 , the stable arenediazonium tetrafluoroborate, ArN 2 + BF 4 − , was prepared. ArN 2 + BF 4 − was then converted to aryl nitrile with crosslinked poly(4‐vinylpyridine) supported cyanide ion in acetonitrile at room temperature. The spent polymeric reagent was regenerated and reused several times without any loss in its activity. This procedure offered advantages, including a higher isolated yield, shorter reaction time, and simple reaction workup. © 2012 Wiley Periodicals, Inc. J Appl Polym Sci, 2012