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Functionalization of Poly(styryllithium) with 1‐Butene Oxide
Author(s) -
Quirk Roderic P.,
Ge Qing,
Arnould Mark A.,
Wesdemiotis Chrys
Publication year - 2001
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/1521-3935(20010601)202:9<1761::aid-macp1761>3.0.co;2-y
Subject(s) - chemistry , surface modification , polystyrene , propylene oxide , polymer chemistry , end group , oxide , size exclusion chromatography , polymer , chemical modification , organic chemistry , copolymer , ethylene oxide , enzyme
Functionalization of poly(styryllithium) with 1‐butene oxide (BO) was studied in benzene at room temperature. The hydroxyl‐functionalized polymer was characterized by size exclusion chromatography (SEC), titration, 1 H NMR, 13 C NMR, DEPT‐ 13 C NMR (distortionless enhancement by polarization transfer) spectroscopy, MALDI‐TOF mass spectrometry and flash column chromatography. The ω ‐hydroxylated polystyrene was obtained in 99% yield with quantitative regioselectivity (addition to the methylene carbon of 1‐butene oxide) to form the secondary alcohol without oligomerization. The amount of unfunctionalized polystyrene formed (< 1%) was much less than that found for functionalization with propylene oxide (PO, 6–7%) consistent with reduced proton transfer from the ethyl group in BO versus the corresponding methyl group in PO.