Anionic Synthesis of Aromatic Carboxyl Functionalized Polymers. Chain-End Functionalization of Poly(styryl)lithium with 4,5-Dihydro-4,4-dimethyl-2- [4-(1-phenylethenyl)phenyl]oxazole

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

• Book ID: 102648231
• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 640 KB
• Volume: 40
• Category: Article
• ISSN: 0959-8103
• DOI: 10.1002/(sici)1097-0126(199606)40:2<79::aid-pi519>3.0.co;2-m

✦ Synopsis

The novel syntheses of 4-(4,5-dihydro-4,4-dimethyl-2-oxazoly1)benzophenone, 1-[4-(4,5-dihydro-4,4-dimethyl-2-oxazoly~)phenyl]-l-phenylethanol and 4,5-dihydro-4,4-dimethyl-2-[4-(1-phenylethenyl)pheny~]oxazole (1) are described.

w-Oxazolyl polystyrene (2) was synthesized in quantitative yields by the reaction of poly(styry1)lithium with stoichiometric amounts of 4,5-dihydro-4,4-dimethyl-2-[4-(l-phenylethenyl)phenyl]oxazole (1) in toluene/tetrahydrofuran (4 : 1 v/v) at -78°C. Deblocking of the oxazoline protecting group by acid hydrolysis followed by saponification 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 ('H NMR, I3C NMR and FTIR), potentiometry and elemental analysis.

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