NDLI: Anionic ring-opening polymerization of five-membered cyclic carbonates derived from aldohexopyranosides

Content Provider	Springer Nature Link
Author	Tezuka, Kunio Koda, Kuniomi Katagiri, Hiroshi Haba, Osamu
Copyright Year	2015
Abstract	To investigate the relationship between the steric structures and polymerizability of five-membered cyclic carbonates, the anionic ring-opening polymerizations of methyl 4,6-O-benzylidene-2,3-O-carbonyl-α-d-galacto- and mannopyranosides (MBCGa and MBGM, respectively), were examined and compared to the results of the already reported glucopyranoside analog (MBCG). The polymerization of MBCGa proceeded without the elimination of CO2 as in the case of MBCG, while MBCM was not polymerized. To estimate the thermodynamic stability of the carbonate rings of these cyclic carbonates, the model reactions using the corresponding hydroxycarbonates were carried out. The ring-closing reactions of the mannopyranoside-based hydroxycarbonate proceeded to produce cyclic carbonate, while the others did not give cyclic carbonates. This should indicate that the carbonate rings of MBCG and MBCGa were less stable than that of MBCM. The single-crystal X-ray structural analysis indicated that the carbonate rings of MBCG and MBCGa have higher angle strains than that of MBCM. This should suggest that the ring strain of the five-membered cyclic carbonate increases by trans-fusing to the pyranose ring.
Starting Page	615
Ending Page	626
Page Count	12
File Format	PDF
ISSN	01700839
Journal	Polymer Bulletin
Volume Number	72
Issue Number	3
e-ISSN	14362449
Language	English
Publisher	Springer Berlin Heidelberg
Publisher Date	2015-01-03
Publisher Place	Berlin, Heidelberg
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Aliphatic polycarbonate Ring-opening polymerization Anionic polymerization X-ray structural analysis Polymer Sciences Soft and Granular Matter, Complex Fluids and Microfluidics Characterization and Evaluation of Materials Physical Chemistry
Content Type	Text
Resource Type	Article
Subject	Chemistry Materials Chemistry Condensed Matter Physics Polymers and Plastics

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