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Synthesis of N ‐aryl azetidine‐2,4‐diones and polymalonamides prepared from selective ring‐opening reactions
Author(s) -
Dai Shenghong A.,
Juang TzongYuan,
Chen ChihPing,
Chang HsinYu,
Kuo WenJang,
Su WenChiung,
Jeng RuJong
Publication year - 2006
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.25126
Subject(s) - azetidine , amine gas treating , reactivity (psychology) , ring (chemistry) , diamine , primary (astronomy) , chemistry , yield (engineering) , aryl , polymer chemistry , organic chemistry , materials science , medicine , physics , alternative medicine , alkyl , pathology , astronomy , metallurgy
Improved high‐yield synthesis of N ‐aryl azetidine‐2,4‐dione has been achieved. The azetidine‐2,4‐dione undergoes ring‐opening reactions with aliphatic primary amines to form malonamide linkages. More importantly, this compound exhibits a high reactivity toward primary aliphatic amine group over alcohols or secondary amines. This selective end‐group functionalization is useful for preparing useful polymer intermediates. In this study polymalonamides were synthesized by fast addition reaction of aliphatic diamine and azetidine‐2,4‐dione. In the meantime, further application for structure‐controlled reaction also has been demonstrated. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 103: 3591–3599, 2007