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Synthesis of Well‐Defined Chain‐End and In‐Chain‐Functionalized Polystyrenes with a Definite Number of α‐Methylstyrene, D ‐Glucose, Phenol, and Benzyl Halide Functionalities by Reactions of Chloro (or Bromo) methylphenyl‐Functionalized Polystyrenes with Substituted 1,1‐Diphenylalkyllithiums
Author(s) -
Hayashi Mayumi,
Hirao Akira
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<1717::aid-macp1717>3.0.co;2-8
Subject(s) - chemistry , polymer chemistry , ethylene , benzyl bromide , phenol , butyllithium , bromide , end group , copolymer , organic chemistry , polymer , catalysis
Chain‐end and in‐chain functionalized polystyrenes with four α‐methylstyrene, eight D ‐glucose, eight phenol, eight benzyl chloride, four benzyl bromide functionalities with well‐defined structures were successfully synthesized by the reactions of well‐defined chain‐end and in‐chain functionalized polystyrenes with four chloro (or bromo)methylphenyl groups and substituted 1,1‐diphenylalkyllithiums. They were prepared from sec ‐butyllithium ( sec ‐BuLi) and the following substituted 1,1‐diphenylethylene derivatives: 1,1‐bis{3‐[(1,2:5,6‐di‐ O ‐isopropylidene‐a‐ D ‐glucofuranose‐ O ‐3‐yl)methyl]phenyl}ethylene ( 1 ), 1,1‐bis(3‐methoxymethylphenyl)ethylene ( 2 ), 1‐{4‐[3‐(4‐isopropenyl‐phenyl)propyl]phenyl}‐1‐phenylethylene ( 3 ), 1,1‐bis(4‐ tert ‐butyldimethylsilyloxyphenyl)ethylene ( 4 ), and 1,1‐bis(3‐ tert ‐butyldimethylsilyloxymethylphenyl) ethylene ( 5 ). In 20 h at –78°C all reactions proceeded cleanly and efficiently in THF to afford quantitatively the expected well‐defined functionalized polystyrenes. Advantages of these reactions are described in this paper.