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Silica‐supported chitosan–osmium tetroxide complex catalyzed vicinal hydroxylation of olefins using hexacyanoferrate(III) ion as a cooxidant
Author(s) -
Huang Kai,
Liu HongWen,
Dou Xi,
Huang MeiYu,
Jiang YingYan
Publication year - 2003
Publication title -
polymers for advanced technologies
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.61
H-Index - 90
eISSN - 1099-1581
pISSN - 1042-7147
DOI - 10.1002/pat.322
Subject(s) - osmium tetroxide , styrene , catalysis , nuclear chemistry , vicinal , yield (engineering) , dihydroxylation , polymer chemistry , osmium , materials science , hydroxylation , ozonolysis , polymer , organic chemistry , chemistry , copolymer , ruthenium , metallurgy , physics , electron microscope , optics , enzyme , enantioselective synthesis
Silica‐supported chitosan–osmium tetroxide complex was prepared by a very simple method. This complex (SiO 2 ‐CS‐OsO 4 ) has been found to be able to catalyze the dihydroxylation of styrene, α‐methyl‐styrene, 1‐heptene, 1‐octene and 1‐decene to get (R)‐(−)‐1‐phenyl‐1,2‐ethanediol, (R)‐(−)‐2‐phenyl‐1,2‐propanediol, (S)‐(−)‐1,2‐heptanediol, (S)‐(−)‐1,2‐octanediol and (R)‐(+)‐1,2‐decanediol in the presence of K 3 Fe(CN) 6 , K 2 CO 3 , t‐BuOH and water at room temperature and under atmospheric pressure. The optical yields amounted to 77.3%, 64.8%, 81.3%, 78.2% and 38.4% respectively, and the product yields were 65.5%, 70%, 89.4%, 51% and 49.6% respectively. The experimental results showed that the OsO 4 content in the SiO 2 ‐CS‐OsO 4 complex greatly affected the optical yield. This new polymer–Os complex was very easy to prepare and could be reused without any appreciable change in optical catalytic activity. Copyright © 2003 John Wiley & Sons, Ltd.