Living cationic-ring-opening polymerization of five-membered cyclic dithiocarbonate controlled by neighboring group participation of carbamate group
Abstract
Abstract A five‐membered cyclic dithiocarbonate having phenylcarbamate moiety 1 underwent cationic ring‐opening polymerization by using methyl trifluoromethanesulfonate as an initiator in nitrobenzene at 60 °C. Both of the corresponding first‐order kinetic plot and conversion‐molecular weight plot showed linearity to suggest the living fashion of the polymerization, which was then supported by two‐stage polymerization experiment. The living fashion as well as the regioselective formation of the repeating unit suggested significant contribution of the neighboring group participation of the carbamate group to form a stabilized cationic propagating end, of which structure was confirmed by performing an equimolar reaction of 1 and methyl trifluoromethanesulfonate with analyzing the resulting species by NMR spectroscopy. © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 4459–4464, 2007
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Protons can initiate polymerization of numerous heterocyclic monomers, including oxiranes, 1,3-dioxolanes, thiiranes, aziridines, tetrahydrofurans, lactones, 1,2-oxazolines and cyclic siloxanes.
“Protons can initiate the polymerization of numerous heterocyclic monomers, e.g., oxiranes, 1,3-dioxolanes, thiiranes, aziridines, tetrahydrofurans, lactones, 1,2 oxazolines and cyclic siloxanes as shown in Figure 16 assuming an activated chain end mechanism, in analogy to Figure 12 (SN2).”
From Ring-Opening Polymerization—An Introductory Review (2013) · cites this paper as [40]
Exchange of an ether side group for an ester or carbamate (neighboring group participation) results in a different, well-defined microstructure during CROP of cyclic dithiocarbonates with methyl triflate initiator due to effective suppression of isomerization of the monomer and stabilization of the growing chain via the ester or carbamate moiety.
“Thus, the exchange of an ether side group for an ester or carbamate (So-called NGP: Neighboring Group Participation) results in a different, well defined, microstructure during the CROP of cyclic dithiocarbonates (Figure 12) with methyl triflate initiator due to effective suppression of the isomerization of the monomer and the stabilization of the growing chain via the ester (carbamate) moiety [40”
From Ring-Opening Polymerization—An Introductory Review (2013) · cites this paper as [40]
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Ring-Opening Polymerization—An Introductory Review
Nuyken, O., & Pask, S. (2013) · Polymers · doi:10.3390/polym5020361 · Cited by 456 · see citing works
“Thus, the exchange of an ether side group for an ester or carbamate (So-called NGP: Neighboring Group Participation) results in a different, well defined, microstructure during the CROP of cyclic dithiocarbonates (Figure 12) with methyl triflate initiator due to effective suppression of the isomerization of the monome…”
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Thiocarbonyl chemistry in polymer science
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- Authors
- Motokucho, S., Sudo, A., & Endo, T.
- Affiliations
- Kindai University (JP)
- Corresponding author
- Endo, Takeshi
- Venue
- Journal of Polymer Science Part A: Polymer Chemistry
- Publisher
- Wiley
- Published
- 2007-08-17
- Volume
- 45
- Issue
- 19
- Pages
- 4459-4464
- ISSN
- 0887-624X (ISSN-L)
- 1099-0518
- OpenAlex
- W2037272538
- Cited by
- 11
- References
- 15
- Citations by year
- 2026: 1 · 2024: 1 · 2023: 1 · 2022: 2 · 2021: 1 · 2020: 2 · 2019: 1 · 2013: 1
- FWCI
- 0.00
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Polymer Science Part A Polymer Chemistry (publishedVersion)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
- Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
- Physical Sciences › Chemistry › Organic Chemistry › Photopolymerization techniques and applications
- Keywords
- cationic ring-opening polymerization, cyclic dithiocarbonates, phenylcarbamates, neighboring group participation, living polymerization, regioselectivity, nitrobenzene solvent, kinetic analysis
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