1109138-89-7Relevant academic research and scientific papers
Selective palladium-catalyzed C-F activation/carbon-carbon bond formation of polyfluoroaryl oxazolines
Yu, Daohong,Shen, Qilong,Lu, Long
, p. 1798 - 1804 (2012/04/04)
A selective palladium-catalyzed Suzuki-Miyaura coupling reaction of polyfluorophenyl oxazolines through ortho C-F activation is described. It was found that reactions with DPPF as the ligand occurred much faster than those with other ligands. A variety of arylboronic acids including challenging functionalized arylboronic acids such as enolizable ketones, aldehyde, cyano, ester, and trifluoromethyl groups were tolerated with the reaction conditions.
Synthesis, microwave-assisted polymerization, and polymer properties of fluorinated 2-phenyl-2-oxazolines: A systematic study
Lobert, Matthias,Thijs, Hanneke M. L.,Erdmenger, Tina,Eckardt, Rebecca,Ulbricht, Christoph,Hoogenboom, Richard,Schubert, Ulrich S.
experimental part, p. 10396 - 10407 (2009/11/30)
We present a detailed systematic study of the synthesis and ability of fluorinated 2-phenyl-2-oxazolines to undergo polymerization. The synthesis of these compounds is based on a two-step procedure that gives the desired 2-oxazolines in moderate-to-good yields. All the compounds were fully characterized by IR and NMR (1H, 13C, and 19F) spectroscopy, mass spectrometry, and elemental analysis. The 2-oxazolines were subsequently used as monomers for living cationic ring-opening polymerization (CROP) with microwave irradiation as the heat source (T= 140°C), nitromethane as the solvent, and methyl tosylate as the initiator. The linear first-order kinetic plots of the polymerizations accompanied by a linear increase of the molecular weight with conversion and low polydispersity index (PDI) values (generally below 1.30) indicate a living polymerization mechanism. The resulting polymerization rates reflect a strong sensitivity to the quantity of fluorine substituents in general and the presence or absence of ortho-fluoro substituents of the phenyl ring in particular. All the polymers were isolated and characterized by size-exclusion chromatography and MALDI-TOF mass spectrometry. Finally, a detailed investigation of selected polymer properties was performed by using differential scanning calorimetry, thermogravimetric analysis, and contact-angle measurements, thus resulting in structure-property relationships. Whereas the thermal properties of the polymers are mostly influenced by the presence of ortho-fluoro substituents, the surface properties are mainly determined by the presence of para- and/or metafluoro substituents.
