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Model reaction for the synthesis of polyhydroxyurethanes from cyclic carbonates with amines: Substituent effect on the reactivity and selectivity of ring‐opening direction in the reaction of five‐membered cyclic carbonates with amine
Abstract
This article focuses on the substituent effect on the reactivity and selectivity of the ring‐opening direction in the reaction of five‐membered cyclic carbonates with n‐hexylamine. The reactivity of the cyclic carbonate and the formation selectivity of the adduct with a secondary hydroxyl group increased as a stronger electron‐withdrawing group was introduced at the α‐methylene of the cyclic carbonate. These results are discussed on the basis of the stability of intermediates, primary and secondary alcoholate anions, Mulliken charges on carbonyl carbon, and the bond lengths and orders of the OCO single bond. © 2001 John Wiley & Sons, Inc. J Polym Sci Part A: Polym Chem 39: 3678–3685, 2001
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Cites
Polylactones 12. Cationic polymerization of 2,2‐dimethyltrimethylene carbonate
Kricheldorf, H. R., Dunsing, R., & Albet, A. S. I. (1987) · Die Makromolekulare Chemie · doi:10.1002/macp.1987.021881020 · Cited by 93
Cited by
Non-isocyanate polyurethanes: from chemistry to applications
Kathalewar, M. S., Joshi, P. B., Sabnis, A. S., & Malshe, V. C. (2013) · RSC Advances · doi:10.1039/c2ra21938g · Cited by 414
Progress in Study of Non-Isocyanate Polyurethane
Guan, J., Song, Y., Lin, Y., Yin, X., Zuo, M., Zhao, Y., Tao, X., & Zheng, Q. (2011) · Industrial & Engineering Chemistry Research · doi:10.1021/ie101995j · Cited by 389
Bähr, M., & Mülhaupt, R. (2012) · Green Chemistry · doi:10.1039/c2gc16230j · Cited by 326
Non-isocyanate polyurethane foams: where we stand and what comes next?
Grignard, B., Bourguignon, M., Monie, F., Vidil, T., Cramail, H., Perli, G., Sardon, H., Raquez, J.-M., Caillol, S., & Detrembleur, C. (2026) · Chemical Society Reviews · doi:10.1039/d5cs00144g · Cited by 12
Metadata
- Authors
- Tomita, H., Sanda, F., & Endo, T.
- Venue
- Journal of Polymer Science Part A: Polymer Chemistry
- Publisher
- Wiley
- Published
- 2001-09-20
- Volume
- 39
- Issue
- 21
- Pages
- 3678-3685
- ISSN
- 0887-624X (ISSN-L)
- 1099-0518
- OpenAlex
- W2047602927
- Cited by
- 226
- References
- 1
- FWCI
- 1.36
- Type
- journal article
- Language
- en
- Open access
- closed
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- Tomita, H., Sanda, F., & Endo, T. (2001). Model reaction for the synthesis of polyhydroxyurethanes from cyclic carbonates with amines: Substituent effect on the reactivity and selectivity of ring‐opening direction in the reaction of five‐membered cyclic carbonates with amine. Journal of Polymer Science Part A: Polymer Chemistry. https://doi.org/10.1002/pola.10009
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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