Premium
Macrocyclic and Polymeric Oxaziridine‐Derivatives
Author(s) -
Dickmeis Marcus,
Cinar Hakan,
Ritter Helmut
Publication year - 2013
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.201200706
Subject(s) - adipate , chemistry , polymer chemistry , diamine , condensation polymer , cyclohexylamine , imine , mass spectrometry , adduct , methylene , bar (unit) , fast atom bombardment , gel permeation chromatography , polymer , organic chemistry , chromatography , catalysis , physics , meteorology
Macrocyclic and polymeric imines 5,5′ and 6,6′ are obtained in excellent yields by template‐free polycondensation of 1,6‐bis(4‐formylbenzoyloxy)hexane (1) with commercially available 4,4′‐methylene‐bis(cyclohexylamine) (2) and with bis(2‐amino‐2‐methylprop‐1‐yl)adipate dihydrochloride (4), respectively. The degree of macrocyclization during imine synthesis strongly depends on the diamine. Matrix‐assisted laser desorption–ionization time‐of‐flight (MALDI‐TOF) mass spectrometry analysis and gel permeation chromatography (GPC) measurements show that (2) leads to more macrocyclic adducts than (4). The subsequent meta ‐chloroperoxybenzoic acid oxidation of polyimines 5,5′ and 6,6′ ( $ \bar M_{\rm n} $ = 1650–11 200 g mol −1 , $ \bar M_{\rm w} $ = 3800–27 350 g mol −1 ) yields the corresponding polyoxaziridines 7,7′ and 8,8′ consisting of macrocyclic and linear polymeric structures ( $ \bar M_{\rm n} $ = 1750–8050 g mol −1 , $ \bar M_{\rm w} $ = 3250–15 800 g mol −1 ). The synthesized polyoxaziridines are relatively stable and storable at room temperature.