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Polymerization of N ‐carboxyanhydrides of 1‐aminocycloalkanecarboxylic acids
Author(s) -
Frankel Max,
Bachi Mario David
Publication year - 1965
Publication title -
biopolymers
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.360030104
Subject(s) - chemistry , polymerization , sodium methoxide , methanol , methoxide , dimethyl sulfoxide , polymer chemistry , alicyclic compound , ring opening polymerization , sodium , polymer , organic chemistry
The polymerizations of the N ‐carboxyanhydrides of 1‐aminocyclopropanecarboxylic acid, 1‐aminocyclobutanecarboxylic acid, 1‐aminocyclopentanecarboxylic acid, and 1‐aminocyclohexanecarboxylic acid were investigated. These N ‐carboxyanhydrides did not polymerize in bulk when heated to their melting points under reduced pressure. In solution, they polymerized extremely slowly on initiation with n ‐hexylamine and relatively slowly when initiated by sodium methoxide–methanol. The polymerization rates of the above NCAs in dimethyl sulfoxide solution, initiated by sodium methoxide–methanol were found to increase in the following order: NCA of 1‐aminocyclohexanecarboxylic acid, NCA of 1‐aminocyclopropanecarboxylic acid, NCA of 1‐aminocyclopentanecarboxylic acid and NCA of 1‐aminocyclobutanecarboxylic acid. The influence of the alicyclic side rings on the relative rates of polymerization of the respective NACs is considered.