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Precision synthesis of (1→6)‐α‐D‐glucopyranan by cationic ring‐opening polymerization of 1,6‐anhydro‐2,3,4‐tri‐ O ‐allyl‐β‐D‐glucopyranose
Author(s) -
Kakuchi Toyoji,
Kusuno Atsushi,
Mori Manami,
Satoh Toshifumi,
Miura Masakatsu,
Sharfuddin Mohd.,
Kaga Harumi
Publication year - 2002
Publication title -
macromolecular symposia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.257
H-Index - 76
eISSN - 1521-3900
pISSN - 1022-1360
DOI - 10.1002/1521-3900(200205)181:1<101::aid-masy101>3.0.co;2-q
Subject(s) - cationic polymerization , polymerization , ring opening polymerization , polymer chemistry , polymer , trifluoromethanesulfonate , chemistry , living polymerization , trimethylsilyl , materials science , radical polymerization , catalysis , organic chemistry
The ring‐opening polymerization of 1,6‐anhydro‐2,3,4‐tri‐ O ‐allyl‐β‐D‐glucopyranose ( 2 ) has been carried out using various cationic initiators. For the condition of [ 2 ]/[BF 3 ·OEt 2 ] = 20 at −15°C for 90 h, the polymer yield, M w and M w / M n of the polymer obtained were 79%, 215,600 and 3.45, respectively. In order to study the living characteristic of the polymerization of 2 , the cationic ring‐opening bulk polymerization initiated by trimethylsilyl trifluoromethanesulfonate (TMSOTf) was carried out under the condition of [ 2 ]/[TMSOTf] = 1000 at −15 °C. The M w value increased in proportion to conversion until c.a. 30% and below. The M w / M n s of resulting polymers were very narrow, e.g., the M w / M n value was 1.2 and below, which was smaller than that for the solution polymerization using BF 3 ·OEt 2 . These results indicated that the ring‐opening bulk polymerization of 2 using TMSOTf was living‐like.