Collect. Czech. Chem. Commun.
2008, 73, 1799-1813
https://doi.org/10.1135/cccc20081799
HFPO Trimer-Based Alkyl Triflate, a Novel Building Block for Fluorous Chemistry. Preparation, Reactions and 19F gCOSY Analysis
Ondřej Kysilkaa, Markéta Rybáčkováa, Martin Skalickýa, Magdalena Kvíčalováb, Josef Cvačkac and Jaroslav Kvíčalaa,*
a Department of Organic Chemistry, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic
b Institute of Inorganic Chemistry, Academy of Sciences of the Czech Republic, v.v.i., Husinec-Řež 1001, 250 68 Řež, Czech Republic
c Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic
Crossref Cited-by Linking
- Chen Xin, Wang Congcong, Gui Wanying, Guo Yong, Zhou Xuming, Zhao Yanbin, Dai Jiayin: Time-course transcriptome analysis discloses PFDMO2OA (C8 HFPO-TA)-induced developmental malformations and cardiovascular toxicities in zebrafish. Environmental Pollution 2024, 347, 123729. <https://doi.org/10.1016/j.envpol.2024.123729>
- Sun Sujie, Zhang Li, Li Xue, Zang Lu, Huang Ling, Zeng Junquan, Cao Zigang, Liao Xinjun, Zhong Zilin, Lu Huiqiang, Chen Jianjun: Hexafluoropropylene oxide trimer acid, a perfluorooctanoic acid alternative, induces cardiovascular toxicity in zebrafish embryos. Journal of Environmental Sciences 2024, 139, 460. <https://doi.org/10.1016/j.jes.2023.05.009>
- Zhu Bao, Sheng Nan, Dai Jiayin: Adverse effects of gestational exposure to hexafluoropropylene oxide trimer acid (HFPO-TA) homologs on maternal, fetal, and placental health in mice. Science of The Total Environment 2024, 912, 169151. <https://doi.org/10.1016/j.scitotenv.2023.169151>
- Li Jia-Wun, Tsai Hui-An, Lee Hsun-Tsing, Cheng Yung-Hsin, Chiu Chih-Wei, Suen Maw-Cherng: Synthesis and properties of side chain fluorinated polyurethanes and evaluation of changes in microphase separation. Progress in Organic Coatings 2020, 145, 105702. <https://doi.org/10.1016/j.porgcoat.2020.105702>
- Li Jia-Wun, Cheng Yung-Hsin, Lee Hsun-Tsing, Tsen Wen-Chin, Chiu Chih-Wei, Suen Maw-Cherng: Properties and degradation of castor oil-based fluoridated biopolyurethanes with different lengths of fluorinated segments. RSC Adv. 2019, 9, 31133. <https://doi.org/10.1039/C9RA04654B>
- Hošek Jan, Šimůnek Ondřej, Lipovská Pavlína, Kolaříková Viola, Kučnirová Kateřina, Edr Antonín, Štěpánková Nikola, Rybáčková Markéta, Cvačka Josef, Kvíčala Jaroslav: Medium Fluorous Separation Using Hydrofluoroether and Weakly Polar Solvents for Environmentally Friendly Recycling of Catalysts. ACS Sustainable Chem. Eng. 2018, 6, 7026. <https://doi.org/10.1021/acssuschemeng.8b00865>
- Li Jia-Wun, Lee Hsun-Tsing, Tsai Hui-An, Suen Maw-Cherng, Chiu Chih-Wei: Synthesis and Properties of Novel Polyurethanes Containing Long-Segment Fluorinated Chain Extenders. Polymers 2018, 10, 1292. <https://doi.org/10.3390/polym10111292>
- Pan Yitao, Zhang Hongxia, Cui Qianqian, Sheng Nan, Yeung Leo W. Y., Guo Yong, Sun Yan, Dai Jiayin: First Report on the Occurrence and Bioaccumulation of Hexafluoropropylene Oxide Trimer Acid: An Emerging Concern. Environ. Sci. Technol. 2017, 51, 9553. <https://doi.org/10.1021/acs.est.7b02259>
- Mukherjee Tathagata, Biswas Soumik, Ehnbom Andreas, Ghosh Subrata K, El-Zoghbi Ibrahim, Bhuvanesh Nattamai, Bazzi Hassan S, Gladysz John A: Syntheses, structures, and stabilities of aliphatic and aromatic fluorous iodine(I) and iodine(III) compounds: the role of iodine Lewis basicity. Beilstein J. Org. Chem. 2017, 13, 2486. <https://doi.org/10.3762/bjoc.13.246>
- Lipovská Pavlína, Rathouská Lucie, Šimůnek Ondřej, Hošek Jan, Kolaříková Viola, Rybáčková Markéta, Cvačka Josef, Svoboda Martin, Kvíčala Jaroslav: Synthesis and catalytic activity of ruthenium complexes modified with chiral racemic per- and polyfluorooxaalkanoates. Journal of Fluorine Chemistry 2016, 191, 14. <https://doi.org/10.1016/j.jfluchem.2016.09.005>
- Hošek Jan, Rybáčková Markéta, Čejka Jan, Cvačka Josef, Kvíčala Jaroslav: Synthesis of Heavy Fluorous Ruthenium Metathesis Catalysts Using the Stereoselective Addition of Polyfluoroalkyllithium to Sterically Hindered Diimines. Organometallics 2015, 34, 3327. <https://doi.org/10.1021/acs.organomet.5b00325>
- Babuněk Mario, Šimůnek Ondřej, Hošek Jan, Rybáčková Markéta, Cvačka Josef, Březinová Anna, Kvíčala Jaroslav: Heavy fluorous phosphine-free ruthenium catalysts for alkene metathesis. Journal of Fluorine Chemistry 2014, 161, 66. <https://doi.org/10.1016/j.jfluchem.2014.03.003>
- Kvíčala Jaroslav, Schindler Martin, Kelbichová Vendula, Babuněk Mario, Rybáčková Markéta, Kvíčalová Magdalena, Cvačka Josef, Březinová Anna: Experimental and theoretical study of Hoveyda–Grubbs catalysts modified by perfluorohexyl ponytail in the alkoxybenzylidene ligand. Journal of Fluorine Chemistry 2013, 153, 12. <https://doi.org/10.1016/j.jfluchem.2013.06.001>
- Skalický Martin, Skalická Veronika, Paterová Jana, Rybáčková Markéta, Kvíčalová Magdalena, Cvačka Josef, Březinová Anna, Kvíčala Jaroslav: Ag Complexes of NHC Ligands Bearing Polyfluoroalkyl and/or Polyfluoropolyalkoxy Ponytails. Why Are Polyethers More Fluorous Than Alkyls?. Organometallics 2012, 31, 1524. <https://doi.org/10.1021/om201062c>
- Bazhin D. N., Gorbunova T. I., Zapevalov A. Ya., Beketov I. V., Saloutin V. I.: A study of the physico-chemical features of the [(perfluoroalkyl)methyl]oxirane amino derivatives based on the hexafluoropropylene oxide trimer. Russ J Gen Chem 2011, 81, 1829. <https://doi.org/10.1134/S1070363211090155>
- Paterová Jana, Skalický Martin, Rybáčková Markéta, Kvíčalová Magdalena, Cvačka Josef, Kvíčala Jaroslav: Synthesis of 2-(perfluoroalkyl)ethyl potassium sulfates based on perfluorinated Grignard reagents. Journal of Fluorine Chemistry 2010, 131, 1338. <https://doi.org/10.1016/j.jfluchem.2010.09.004>
- Nemes Anikó, Tölgyesi László, Bodor Andrea, Rábai József, Szabó Dénes: Greener fluorous chemistry: Convenient preparation of new types of ‘CF3-rich’ secondary alkyl mesylates and their use for the synthesis of azides, amines, imidazoles and imidazolium salts. J FLUORINE CHEM 2010, 131, 1368. <https://doi.org/10.1016/j.jfluchem.2010.10.001>
- Kysilka Ondrej, Rybackova Marketa, Skalicky Martin, Kvicalova Magdalena, Cvacka Josef, Kvicala Jaroslav: ChemInform Abstract: HFPO Trimer‐Based Alkyl Triflate, a Novel Building Block for Fluorous Chemistry. Preparation, Reactions and 19F gCOSY Analysis. ChemInform 2009, 40. <https://doi.org/10.1002/chin.200921049>
- Kysilka Ondřej, Rybáčková Markéta, Skalický Martin, Kvíčalová Magdalena, Cvačka Josef, Kvíčala Jaroslav: Fluorous imidazolium room-temperature ionic liquids based on HFPO trimer. Journal of Fluorine Chemistry 2009, 130, 629. <https://doi.org/10.1016/j.jfluchem.2009.04.006>
- Skalický Martin, Rybáčková Markéta, Kysilka Ondřej, Kvíčalová Magdalena, Cvačka Josef, Čejka Jan, Kvíčala Jaroslav: Synthesis of bis(polyfluoroalkylated)imidazolium salts as key intermediates for fluorous NHC ligands. Journal of Fluorine Chemistry 2009, 130, 966. <https://doi.org/10.1016/j.jfluchem.2009.07.015>