Syntheses and polymerizations of some vinyl monomers containing nitro- or fluorophthalimides

4-Nitro- N -vinylphthalimide (4) was synthesized by two different procedures. Compound 4 was not polymerizable or copolymerizable by AIBN. Poly(N -vinylphthalimide) (17) was prepared and partially nitrated at 10-25°C. N, N 2 (1,2-Ethanediyl)bis(4-nitrophthalimide) (15) and N, N 2 (1,3-propanediyl)bis(4-nitrophthalimide) (16) were prepared by the condensation of the corresponding diamine with phthalic anhydride followed by nitration of the condensation products. 4-Nitrophthalic anhydride was prepared by the hydrolysis of 15 . Four styrene-substituted phthalimide monomers were synthesized. These include N -(4-vinylphenyl)phthalimide (25a), N -(4-vinylphenyl)-3-fluorophthalimide (25b), N -(4-vinylphenyl)-3-nitrophthalimide (25c), and N -(4-vinylphenyl)-4-nitrophthalimide (25d). Monomers 25a and 25b were polymerized by freeradical initiator (AIBN), whereas monomers 25c and 25d were not polymerizable or copolymerizable by AIBN due to a strong inhibitive effect exerted by the nitrophthalimide group. Monomers 25c and 25d were cationically polymerized (BF 3 ·OEt 2). Monomer 25b and styrene were copolymerized and their reactivity ratios were r 1 = 1.7 and r 2 = 0.55, respectively. The prepared polymers are useful as backbone polymers for grafting living anionic polymers.