Beilstein J. Org. Chem.2014,10, 902–909, doi:10.3762/bjoc.10.88
acid yielding isosorbide diacrylate (9a) and isosorbide dicrotonate (9b), which were reacted with benzaldehyde oxime in the presence of zinc(II) iodide and boron triflouride etherate as catalysts to obtain N-alkylated dinitrones 10a/b. Poly(isosorbide itaconite -co- succinate) 13 as a bio-based
unsaturated polyester was cross-linked by a 1,3-dipolar cycloaddition with the received dinitrones 10a/b. The 1,3-dipolar cycloaddition led to a strong change of the mechanical properties which were investigated by rheological measurements. Nitrones derived from methyl acrylate (3a) and methyl crotonate (3b
) were used as model systems and reacted with dimethyl itaconate to further characterize the 1,3-dipolaric cycloaddition.
Keywords: bio-based polyesters; cross-linkers; dinitrones; 1,3-dipolar cycloaddition; isosorbide; Introduction
Nitrones represent a class of compounds with a versatile use as
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Graphical Abstract
Scheme 1:
Synthesis of Z-configurated model compounds 3a/b from E-benzaldoxime and acrylates 2a/b.