Polymeric nitrones, 1. Synthesis and modification of polymeric nitrones derived from polymerizable aldehydes

The model compound N,C-diphenylnitrone[N-(benzylidene)aniline-N-oxide] (3) was prepared by condensation of benzaldehyde with phenylhydroxylamine to study its thermal stability. X-ray diffraction analysis of a single crystal established the conformation of the nitrone group. A new monomer 4-(methacryloyloxy)benzaldehyde-phenylnitrone (8) was also prepared and could not be polymerized with 2,2′-azobisisobutyronitrile (AIBN) as initiator at 70°C. Under these conditions the nitrone reacted exclusively in an intermolecular 1,3-dipolar cycloaddition to give oligomeric tetrahydro-1,2-oxazoline derivates. The kinetics of the cycloaddition was investigated. Additionally, different (meth)acryl- and s…