Fluoride Ion Initiated Reactions of Perfluoro α-Olefins. III. The Condensation of Perfluoro α-Olefins with Carbon Dioxide to Yield Perfluoro Carboxylic Acids

The effect of oxygen in the photocatalytic oxidation pathways of perfluorooctanoic acid

“…This transition confirmed the coexistence of comparable amounts of different perfluorocarboxylic acids (C 8-3 ). In addition, the presence of TFA (C 2 ) was also proved by its distinctive signal at -76.55 ppm to low concentration of shorter perfluorocarboxylic acids [55][56][57][58][59][60][61]. In N 2 test at 15 h and in Air test at 7 h, only a broadening of the intense signal of the CF 2(α-ζ) peaks was observed.…”

“…3-A). In the spectra of Air test at 15 h and O 2 test at both 7 and 15 h, the well-resolved triplet of triplets of the PFOA CF 3(η) signal at -81.86 ppm varied in multiple signals resulting from the partial overlapping of several contributions: a triplet at -82.15 ppm due to PFPrA, a triplet of triplets at -82.03 ppm due to PFPeA and a multiplet in the range between -81.86 and -81.92 ppm due to overlapping triplets of triplets ascribable to PFOA, PFHpA, PFHxA and PFBA [55][56][57][58][59][60][61]. This transition confirmed the coexistence of comparable amounts of different perfluorocarboxylic acids (C 8-3 ).…”

A novel and efficient synthetic route to perfluoroisobutyronitrile from perfluoroisobutyryl acid

“…The main impurity was found to be the raw material itself when the temperature was below 60 C. Below 60 C, most of the 1 will decompose to form hexauoropropylene (HFP) in the distillation step. 17 This would ultimately reduce the quantity of 1. In contrast, if the temperature exceeded 70 C or higher, most of raw materials was lost during the reaction.…”

Synthesis of Perfluoroalkyl-Substituted Azines via Nucleophilic Substitution of Hydrogen with Perfluoroisopropyl Carbanions

“…m,Ph),m,Ph), 7.46 (1H, s, NCHdCCOCF 3 ); 13 C NMR (100 MHz) δ 33.5 (d, 2 J CF ) 21. 5 Hz),71.2,90.5 (m), 98.0, 101.5, 117.0 (q, 1 J CF ) 291.4 Hz), 121.0 (dm, 1 J CF ) 288.0 Hz), 128.2, 128.4, 128.9, 128.9, 129.2, 129.3, 131.6, 136.8, 137.0, 146.6 (d, 4 J CF ) 5.1 Hz), 177.5 (q, 2 J CF ) 33.7 Hz); 19 F NMR (376 MHz) δ -183.27 (1F, m, CF(CF 3 ) 2 ), -75.62 (3F, m, 3 J FF ) 8.3 Hz, CF-(CF 3 ) 2 ), -73.24 (3F, m, 3 J FF ) 7.6 Hz, CF(CF 3 ) 2 ), -69.7 (3F, s, COCF 3 ); MS (EI 70 eV, m/z, %) 511 (M + , <1), 342 (10), 167 (100), 165 (17) 13 C NMR (50 MHz) δ 21.0 (d, 4 J CF ) 5.5 Hz), 42.5 (d, 2 J CF ) 20.9 Hz), 57.1, 89.5 (d, 3 J CF ) 9. 5 Hz),101.5,127.2,127.6,128.7,130.3,134.0,137.9.…”

“…Polyfluorinated alkenes readily add fluoride anions and other nucleophiles leading to the formation of perfluorocarbanions. , Synthetic application of these intermediates is partially impeded by the competing fluoride-catalyzed oligomerization of the starting fluoroalkenes; however, there are reports on their successful reactions with electrophiles such as alkyl 14 and acyl 15 halides, chloromethyl ethers, carbon dioxide, HgCl 2 , etc. Their potential use in nucleophilic perfluoroalkylation of heteroaromatic compounds was explored only in a very specific case of perfluorinated aromatics (mainly pyridines) by Chambers and co-workers .…”