H. Ritter et R. Sperber, POLYMERIZABLE MESOIONS .2. RADICAL POLYMERIZATION AND 1,4-DIPOLAR POLYCYCLOADDITION OF A 4-VINYLPHENYL-MODIFIED MESOIONIC 4,6-DIOXO-1,3-DIAZINE, Macromolecular rapid communications, 16(6), 1995, pp. 407-415
Mesoionic l-4,6-dioxo-3-phenyl-1-(4-vinylphenyl)-1,3-diazine (5) was o
btained by condensation of 3-phenyl-1-(4-vinylphenyl)formamidine (3) w
ith methylmalonic acid (4). This vinyl-substituted mesoionic heterocyc
lic compound was polymerized by usual radical initiation and, addition
ally, by thermally controlled polycycloaddition in solution, yielding
two different types of polymers, 6, 7. According to the X-ray diffract
ion analysis, the structure of a low molecular weight model proves the
regioselectivity of the polycycloaddition.