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Optically active polyethers from chiral terminal epoxides with bulky group
Author(s) -
Cao Jing,
Yang NianFa,
Wang PangDeng,
Yang LiWen
Publication year - 2008
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/pi.2380
Subject(s) - substituent , polymer chemistry , chemistry , polymerization , asymmetric carbon , oxide , copolymer , methacrylate , polymer , optically active , asymmetric induction , organic chemistry , catalysis , enantioselective synthesis
Abstract BACKGROUND: Although the backbone of polyethers from epoxides is flexible and less rigid in solution, we try to determine whether chiral terminal epoxides could form single‐handed helical coiling in solution with the introduction of a bulky group at the 3‐carbon that may fix the helix sense through the large interaction between pendants. RESULTS: Several chiral terminal epoxides with bulky groups at the 3‐carbon such as ( S )‐4,4,4‐triphenyl‐1‐butene oxide (( S )‐TPBO), ( S )‐4,4‐diphenyl‐1‐butene oxide, ( S )‐4‐benzyl‐4,4‐diphenyl‐1‐butene oxide and ( S )‐4,4‐diphenyl‐1‐nonene oxide were synthesized and polymerized. Except for poly[( S )‐TPBO], the polyepoxides could not retain a stable helical conformation in solution. CONCLUSION: The conformation and length of polymers were directly related to the bulky substituent on the 3‐carbon of chiral epoxides, and if the bulkiness and rigidity of the substituent were appropriate, the helical conformation of the polyethers formed could be retained in solution. Optically active polyethers would be potential substitutes for optically active poly(triphenylmethyl methacrylate) due to their much greater hydrolytic resistance. Copyright © 2007 Society of Chemical Industry