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Abstract
A simple and modular dialkylation of two electron-rich pyridine derivatives, namely 4-aminopyridine or 1,2,3,4-tetrahydropyrido[3,4-b]pyrazine, is achieved by aza-Michael reactions with electron-poor olefins (ethyl acrylate and acrylonitrile). Reducing the ester groups in the ethyl acrylate-derived compounds yielded the corresponding hydroxyl-containing derivatives. Subsequently, homopolymerization of phenyl glycidyl ether as well as an epoxy-alcohol polyaddition are catalyzed using the introduced compounds. As a reference catalyst, 4-dimethylaminopyridine is used. It is found that in all cases an irreversible termination of the polymerization at temperatures above 100 °C occurred. The decomposition is particularly rapid in the case of pyridine derivatives containing hydroxyl groups. In contrast, at a constant temperature of 100 °C, the latter compounds gave the fastest phenyl glycidyl ether homopolymerization and high conversions are found for all electron-rich pyridine derivatives. However, testing the catalysts at high alcohol concentrations at temperatures higher than 100 °C resulted in similarly moderate conversions in all cases.
Original language | English |
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Article number | 2300299 |
Journal | Macromolecular Chemistry and Physics |
Volume | 225 |
Issue number | 2 |
Early online date | 22 Nov 2023 |
DOIs | |
Publication status | E-pub ahead of print - 22 Nov 2023 |
Keywords
- 4-dimethylaminopyridine
- aza-Michael reaction
- epoxy-homopolymerization
ASJC Scopus subject areas
- Condensed Matter Physics
- Materials Chemistry
- Polymers and Plastics
- Physical and Theoretical Chemistry
- Organic Chemistry
Fields of Expertise
- Advanced Materials Science
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