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Facile synthesis of phenyl‐capped oligoanilines using pseudo‐high dilution technique
Author(s) -
Gao Junbo,
Li Ke,
Zhang Wanjin,
Wang Ce,
Wu Zhongwen,
Ji Yiping,
Zhou Yao,
Shibata Mitsuhiro,
Yosomiya Ryutoku
Publication year - 1999
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/(sici)1521-3927(19991001)20:10<560::aid-marc560>3.0.co;2-a
Subject(s) - diphenylamine , ammonium persulfate , phenylhydrazine , chemistry , dilution , acetaldehyde , deprotonation , hydrochloric acid , hydrolysis , ammonium , organic chemistry , polymer chemistry , polymerization , ethanol , ion , physics , thermodynamics , polymer
Monodispersed phenyl‐capped trianiline and tetraaniline were successfully synthesized by the reactions of diphenylamine with acetaldehyde‐based Schiff's bases of N ‐phenyl‐1,4‐phenylenediamine and 1,4‐phenylenediamine, respectively, in the presence of ammonium persulfate and hydrochloric acid, subsequent deprotonation and reduction with phenylhydrazine. The reaction mechanism probably involves the slow hydrolysis of the Schiff's bases and subsequent oxidative coupling reactions of the formed ammonium salts with diphenylamine at pseudo‐high dilution condition of the salts.