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From Polyesters to Polyamides Via ON Acyl Migration: An Original Multi‐Transfer Reaction
Author(s) -
Tailhades Julien,
Blanquer Sébastien,
Nottelet Benjamin,
Coudane Jean,
Subra Gilles,
Verdié Pascal,
Schacht Etienne,
Martinez Jean,
Amblard Muriel
Publication year - 2011
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/marc.201100235
Subject(s) - polyester , polyamide , monomer , polymer chemistry , polymerization , derivative (finance) , polymer , chemistry , aqueous solution , interfacial polymerization , organic chemistry , materials science , financial economics , economics
A new strategy for the synthesis of polyamides from polyesters of hydroxyl‐containing amino acids using a multi ON acyl transfer reaction was developed. This original approach allowed the synthesis of three generations of polymers from the same starting monomer. The polymerization of N ‐benzyloxycarbonyl‐serine and its γ‐homologated derivative provided the Z‐protected polyesters; then the water‐soluble polycationic polyesters were obtained by removal of the Z‐protecting group; and finally the polyamides were obtained by a base‐induced multi ON acyl transfer, both in aqueous or organic medium. The key step transfer reaction was monitored by the disappearance and appearance of characteristic NMR proton signals and IR bands of polyesters and polyamides.