Macrocyclic and Polymeric Oxaziridine-Derivatives

作者：Dickmeis Marcus; Cinar Hakan; Ritter Helmut^*

来源：Macromolecular Rapid Communications, 2013, 34(3): 263-268.

DOI：10.1002/marc.201200706

• heteroatom-containing polymers
• macrocycles
• nitrones
• polyimines
• polyoxaziridines

Macrocyclic and polymeric imines 5,5%26apos; and 6,6%26apos; are obtained in excellent yields by template-free polycondensation of 1,6-bis(4-formylbenzoyloxy)hexane (1) with commercially available 4,4%26apos;-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%26apos; and 6,6%26apos; ((M) over bar (n) = 1650-11 200 g mol(-1), (M) over bar (w) = 3800-27 350 g mol(-1)) yields the corresponding polyoxaziridines 7,7%26apos; and 8,8%26apos; consisting of macrocyclic and linear polymeric structures ((M) over bar (n) = 1750-8050 g mol(-1), (M) over bar (w) = 3250-15 800 g mol(-1)). The synthesized polyoxaziridines are relatively stable and storable at room temperature.

• 出版日期2013-2-12