Synthesis and polymerization of N‐[4‐N′‐ (α‐methylbenzyl)aminocarbonylphenyl]maleimide

Abstract

AbstractA novel type of optically active N‐[4‐N′‐(α‐methylbenzyl)aminocarbonylphenyl]maleimide [(R)‐MBCP] was synthesized from maleic anhydride, p‐aminobenzoic acid, and (R)‐methylbenzylamine. Radical homopolymerization of (R)‐MBCP was performed in tetrahydrofuran (THF) at 50 and 70°C for 24 h to give optically active polymers having [α]25D = ‐141° and ‐129°, respectively. Anionic polymerization of (R)‐MBCP with n‐butyllithium in THF and N,N‐dimethylformamide gave an optically active polymer having −78 to −81° of [α]25D. Radical copolymerizations of (R)‐MBCP (M1) were performed with styrene (ST, M2) and methyl methacrylate (MMA, M2) in THF at 50°C. The monomer reactivity ratios (r1, r2) and the Alfrey‐Price Q‐e values were determined as follows: r1 = 0.009, r2 = 0.091, Q1 = 1.30, e1 = 1.87 in the (R)‐MBCP‐ST; r1 = 0.27, r2 = 1.21, Q1 = 0.93, e1 = 1.46 in the (R)‐MBCP‐MMA system. Chiroptical properties of the polymers were also investigated. © 1992 John Wiley & Sons, Inc.