Anionic synthesis of aromatic amide and carboxyl functionalized polymers. Chain-end functionalization of poly(styryl)lithium withN,N-diisopropyl-4-(1-phenylethenyl)benzamide

Abstract

The novel syntheses of N,N-diisopropyl-4-benzoylbenzamide, N,N-diisopropyl-4-(1-hydroxy-1-phenylethyl)benzamide, and N,N-diisopropyl-4-(1-phenylethenyl)benzamide (1) are described. ω-Amidopolystyrene (2) was synthesized in quantitative yields by the reaction of poly(styryl)lithium with stoichiometric amounts of N,N-diisopropyl-4-(1-phenylethenyl)benzamide (1) in toluene/tetrahydrofuran (4 : 1 v/v) at −78°C. Deblocking of the amide protecting group by acid hydrolysis quantitatively provides the corresponding aromatic carboxyl chain-end functionalized polystyrene (3). The functionalization agent and functionalized polymers were characterized by HPLC, thin-layer chromatography, size exclusion chromatography, vapor phase osmometry, spectroscopy (1H-NMR, 13C-NMR, and FTIR), potentiometry, and elemental analysis. © 1998 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 36: 1233–1241, 1998