Does the oxa-Michael reaction of 2-trifluoromethacrylic acid lead to fluorinated polyesters?
Literature Information
Minh-Loan Tran-Do, Nadim Eid, Cédric Totée, Olinda Gimello, Bruno Améduri
2-Trifluoromethacrylic acid (MAF) is a peculiar fluorinated functional monomer. Though it is known to polymerise via CC bond cleavage under anionic initiation, its oxa-Michael addition polymerisation afforded polyesters bearing trifluoromethyl side groups. This oxa-Michael addition was attempted in the presence of radical (peroxides), basic (amines and phosphines) and acidic (AlCl3, triflic acid, and p-toluenesulfonic acid) reactants and catalysts which led to the formation of oligomers with various yields (up to 57%) and molar masses (up to 2200 g mol−1). The obtained polyesters were characterised by GC/MS, IR, 19F NMR, 1H NMR and 13C NMR spectroscopy techniques and MALDI-TOF, and their thermal properties were determined by thermogravimetric analysis and differential scanning calorimetry. Triphenylphosphine and piperidine led to the highest degree of polymerization DPn (up to the 16th adduct) with a degradation temperature of about 200 °C. The glass transition temperatures (Tg) were −59 and −46 °C for the MAF bisadduct (diMAF) and oligoMAF, respectively. Such oligomers were hydrophobic, evidenced by a water contact angle measurement of 107°, showing that the contribution of the trifluoromethyl group was higher than that of the ester function.
Related Literature
Unprecedented steric deformation of ortho-carborane
Brian W. Hutton, Fraser MacIntosh, David Ellis, Fabien Herisse, Stuart A. Macgregor, David McKay, Victoria Petrie-Armstrong, Georgina M. Rosair, Dmitry S. Perekalin, Hugo Tricas, Alan J. Welch
DOI: 10.1039/B810702E
Enantiomerically purebicyclo[3.3.1]nona-2,6-diene as the sole source of enantioselectivity in BIPHEP-Rh asymmetric hydrogenation
Tharmalingam Punniyamurthy, Monika Mayr, Alexander S. Dorofeev, Carole J. R. Bataille, Silvia Gosiewska, Bao Nguyen, Andrew R. Cowley, John M. Brown
DOI: 10.1039/B807669C
Rhodium-catalysed cyclisation reaction of allenynes with arylboronic acids
Tomoya Miura, Keita Ueda, Yusuke Takahashi, Masahiro Murakami
DOI: 10.1039/B810665G
Covalent surface modification of a metal–organic framework: selective surface engineering viaCuI-catalyzed Huisgen cycloaddition
Tendai Gadzikwa, Guang Lu, Charlotte L. Stern, Scott R. Wilson, Joseph T. Hupp, SonBinh T. Nguyen
DOI: 10.1039/B805101A
A general precipitation strategy for large-scale synthesis of molybdate nanostructures
Cheng Peng, Lian Gao, Songwang Yang, Jing Sun
DOI: 10.1039/B812033A
Quantifying the fraction of glycine and alanine in β-sheet and helical conformations in spider dragline silk using solid-state NMR
Gregory P. Holland, Janelle E. Jenkins, Melinda S. Creager, Randolph V. Lewis, Jeffery L. Yarger
DOI: 10.1039/B812928B
Crystallographic characterization and identification of a minor isomer of C84fullerene
Lars Epple, Konstantin Amsharov, Kalin Simeonov, Ina Dix, Martin Jansen
DOI: 10.1039/B811872H
Cymantreneconjugation modulates the intracellular distribution and induces high cytotoxicity of a cell-penetrating peptide‡
Ines Neundorf, Jan Hoyer, Katrin Splith, Robert Rennert, Harmel W. Peindy N’Dongo, Ulrich Schatzschneider
DOI: 10.1039/B812799A
Functional biomimetic models for the active site in the respiratory enzyme cytochrome c oxidase
James P. Collman, Richard A. Decréau
DOI: 10.1039/B808070B
Sonication treatment of CdTe/CdS semiconductor nanocrystals and their bio-application
Kyung Nam Kim, Pan Kee Bae, Hyun Ju Chang, Yong-Rok Kim, Joung Kyu Park
DOI: 10.1039/B812317A
You might also like
What are the main uses of 1H-Indazole-6-carbonitrile (CAS: 141290-59-7)?
1H-Indazole-6-carbonitrile finds applications in pharmaceuticals, where it serve...
How should waste containing Dioctyl (2E)-2-butenedioate (CAS: 2997-85-5) be handled?
Waste containing Dioctyl (2E)-2-butenedioate (CAS: 2997-85-5) should be collecte...
What industries use Sodium [(1,2-benzoxazol-3-ylmethyl)sulfonyl]azanide (CAS: 68291-98-5)?
Sodium [(1,2-benzoxazol-3-ylmethyl)sulfonyl]azanide is primarily used in pharmac...
Are there alternatives to Dimethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,6-pyridinedicarboxylate (CAS: 741709-66-0) in synthesis?
Dimethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,6-pyridinedicarboxyla...
How should waste containing 2-Fluoro-6-hydrazinopyridine (CAS: 80714-39-2) be handled?
Waste containing 2-Fluoro-6-hydrazinopyridine (CAS: 80714-39-2) should be manage...
What is 6-Formyl-2-pyridinecarboxylic acid (CAS: 499214-11-8)?
6-Formyl-2-pyridinecarboxylic acid is an organic compound with the molecular for...
What is the market or research trend for 3-(3,4-dimethoxyphenyl)-2,5-dimethyl-N-(2-morpholin-4-ylethyl)pyrazolo[1,5-a]pyrimidin-7-amine (CAS: 900874-91-1)?
Research trends for this compound indicate a focus on its potential applications...
How is 9H-Tribenzo[b,d,f]azepine (CAS: 29875-73-8) typically synthesized?
9H-Tribenzo[b,d,f]azepine is typically synthesized via a multi-step process invo...
How is 1-Cyclopropyl-7-ethoxy-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid (CAS: 1797982-51-4) typically synthesized?
1-Cyclopropyl-7-ethoxy-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxyli...
How should waste containing Methyl 3-oxo-1,2,3,4-tetrahydro-6-quinoxalinecarboxylate (CAS: 671820-52-3) be handled?
Waste containing Methyl 3-oxo-1,2,3,4-tetrahydro-6-quinoxalinecarboxylate (CAS: ...
Source Journal
Polymer Chemistry

Polymer Chemistry welcomes submissions in all areas of polymer science that have a strong focus on macromolecular chemistry. Manuscripts may cover a broad range of fields, yet no direct application focus is required.










![2-Methyl-2-propanyl 4-{2-fluoro-5-[(4-oxo-3,4-dihydro-1-phthalazinyl)methyl]benzoyl}-1-piperazinecarboxylate structure 2-Methyl-2-propanyl 4-{2-fluoro-5-[(4-oxo-3,4-dihydro-1-phthalazinyl)methyl]benzoyl}-1-piperazinecarboxylate structure](https://static.chemtradehub.com/structs/763/763114-04-1-65a9.webp)
![(3aS,6aS)-1-Methyloctahydropyrrolo[3,4-b]pyrrole structure (3aS,6aS)-1-Methyloctahydropyrrolo[3,4-b]pyrrole structure](https://static.chemtradehub.com/structs/877/877212-98-1-9157.webp)


