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

✍ Scribed by Gabriel J. Summers; Roderic P. Quirk

• Book ID: 101273003
• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 310 KB
• Volume: 36
• Category: Article
• ISSN: 0887-624X
• DOI: 10.1002/(sici)1099-0518(199806)36:8<1233::aid-pola5>3.0.co;2-0

✦ Synopsis

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. v-Amidopolystyrene ( 2) was synthesized in quantitative yields by the reaction of poly(styryl)lithium with stoichiometric amounts of N,Ndiisopropyl-4-(1-phenylethenyl)benzamide ( 1) in toluene/tetrahydrofuran (4 : 1 v/v) at 078ЊC. 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 ( 1 H-NMR, 13 C-NMR, and FTIR), potentiometry, and elemental analysis.