title: Macrocyclic and polymeric oxaziridine-derivatives.
abstract: 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.
authors: Institut für Organische Chemie und Makromolekulare Chemie II, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, 40225 Düsseldorf, Germany.
authors: Marcus
authors: M
authors: Dickmeis
authors: Hakan
authors: H
authors: Cinar
authors: Helmut
authors: H
authors: Ritter
mesh_terms: D001388:Aziridines / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D058105:Polymerization; D011108:Polymers / Q000737:chemistry*
chemical_list: D001388:Aziridines; D011108:Polymers; C033132:aziridine