Well‐defined poly(3‐alkyl‐4‐benzamide) was synthesized by means of chain‐growth condensation polymerization of phenyl 3‐octyl‐4‐(4‐octyloxybenzyl(OOB)amino)benzoate (1c) from initiator 2, followed by removal of the OOB groups on amide nitrogen of poly1c. Polymerization of 1c with phenyl 4‐(trifluoromethyl)benzoate (2b) in the presence of 1,1,1,3,3,3‐hexamethyldisilazide (LiHMDS) and LiCl in THF at −10 °C gave poly1c with a narrow molecular weight distribution (Mw/Mn ≤ 1.08) and a well‐defined molecular weight (Mn = 4480–12,700) determined by the feed ratio of monomer to initiator (from 10 to 30). The OOB groups of poly1c were removed with H2SO4 to give the corresponding N‐unsubstituted poly(p‐benzamide) (poly1c′) with low polydispersity. The solublity of poly1c′ in polar organic solvents was dramatically higher than that of poly(p‐benzamide), demonstrating that introduction of an alkyl group on the aromatic ring is very effective for improving the solubility of poly(p‐benzamide). © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 360–365

To successively construct two amide bonds between two benzene rings, the reaction of methyl N-alkylanthranilate and N-alkylisatoic anhydride in the presence of a base was studied. When the reaction was carried out with lithium hexamethyldisilazide and N,N,N′,N′-tetramethylethylenediamine in THF at 70 °C under reduced pressure, a cyclic diamide was obtained in high yield.

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