A more convenient synthesis of the perfluoro alkyl hypofluorite (F C) COF as well as the hitherto unknown (C F )(F C) COF compound is reported. Both hypofluorites can be prepared by use of the corresponding tertiary alcohols R OH and elemental fluorine in the presence of CsF. An appropriate access to these highly reactive hypofluorites is crucial. The hypofluorites are then transferred into their corresponding perfluoro bisalkyl peroxides R OOR [R =(F C) C, (C F )(F C) C] by treatment with partially fluorinated silver wool. NMR, gas-phase infrared, and solid-state Raman spectra of the perfluoro bisalkyl peroxides are presented and their chemical properties are discussed.
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http://dx.doi.org/10.1002/chem.201903620 | DOI Listing |
Org Lett
January 2025
Laboratory of Catalysis and Organic Synthesis, Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247667, Uttarakhand, India.
Herein, we have reported the application of bench stable perfluoroalkanoic acids as fluoro-alkylating reagents in combination with DIB and primary amides for sequential one-pot transformation to R-embedded functionalized amides under metal-free conditions. The protocol is tolerant to a range of sensitive functional groups (>33 examples and up to 90% yield), and perfluoro acids. Preliminary mechanistic studies, control experiments, in situ F-NMR analyses, and the synthesis of intermediate species were performed to understand the reaction pathways.
View Article and Find Full Text PDFChemistry
November 2024
Institute of Chemistry and Biochemistry, Freie Universität Berlin, Takustrasse 3, 14195, Berlin, Germany.
The self-assembly process is governed by the individual constituents of molecules through precise non-covalent interactions. Amphiphilic cyanines are intriguing in supramolecular chemistry due to the large polarizability of their delocalized π-electron systems, their tuneable optical properties and their ability to form well-defined self-assembled structures in different media. Here we present the synthesis of a novel tetrahydroxy amphiphilic carbocyanine dye with perfluoro alkylated chains -(CH)-(CF)-CF as hydrophobic segments and aminoproanediol as hydrophilic segment.
View Article and Find Full Text PDFJ Hazard Mater
December 2024
Princeton University, United States. Electronic address:
Per- and polyfluoroalkyl substances (PFAS) have emerged as a diverse class of environmental pollutants, garnering increasing attention due to their various structural types and potential ecological impacts. The impact of select PFAS on environmental microorganisms and the potential for microbial degradation of certain PFAS are timely research topics. In this study, we conducted a series of batch incubation to investigate the effects of C-C perfluoroalkyl carboxylic acids (PFCAs) and perfluorosulfonic acids (PFSAs), as well as linear and branched perfluorooctanoic acid (PFOA) and perfluorooctanesulfonic acid (PFOS) monomers, on the Feammox reaction and Acidimicrobium sp.
View Article and Find Full Text PDFEnviron Geochem Health
September 2024
Department of Medicinal and Applied Chemistry, Kaohsiung Medical University (KMU), Kaohsiung, 807, Taiwan.
J Hazard Mater
September 2024
Aarhus University Centre for Water Technology (WATEC), Aarhus University, Aarhus C, Denmark; Department of Biological and Chemical Engineering, Aarhus University, Aarhus C, Denmark. Electronic address:
Hydrothermal liquefaction (HTL) is a promising technology for converting wet organic waste such as sewage sludge into biocrude oil while simultaneously destroying per- and polyfluoroalkyl substances (PFAS). This study tracked the fate and degradation of six representative PFAS in water to address the effect of perfluoroalkyl chain length on degradation rates and the formation of volatile transformation products at 300-350 °C. While perfluorosulfonic acids were recalcitrant, perfluoroalkyl carboxylic acids (PFCAs) were rapidly and completely decarboxylated to hydroperfluoroalkanes (1 H-perfluoroheptane in the case of perfluorooctanoic acid).
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