A general method for the preparation of perfluoroalkanesulfonyl chlorides

Scott, Peter J. H.; Campbell, Ian B.; Steel, Patrick G.

doi:10.1016/j.jfluchem.2005.05.007

Cited by 7 publications

(7 citation statements)

References 15 publications

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“…Evaporation of the solvent afforded 6 as a colourless solid; yield: 531 mg (1.77 mmol,>99%). All spectral data are in accordance with previous reports 38 . 19 F NMR (CD 3 OD, 282 MHz): δ =−127.6 (s, 2 F), −123.8 (s, 2 F), −116.3 (s, 2 F), −82.9 (d, J =6.4 Hz, 3F).…”

Section: Methodssupporting

confidence: 78%

Manufacture and characterisation of thin flat and curved auxetic foam sheets

Alderson

Ravirala

et al. 2012

Physica Status Solidi (b)

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A series of gold(I) isonitrile complexes were prepared and converted to the corresponding diaminocarbene gold(I) complexes by reactions with primary and symmetrical secondary amines. Twelve crystal structure analyses of the gold(I) complexes could be obtained, in addition NMR studies allowed an analysis of the different diastereomers present in solution. In the gold‐catalyzed phenol synthesis these complexes were very successful as pre‐catalysts, reaching an unprecedented 3050 turnovers with a problematic substrate. Good conversions in the hydration of phenylacetylene could also be achieved.

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Section: Methodssupporting

confidence: 78%

Manufacture and characterisation of thin flat and curved auxetic foam sheets

Alderson

Ravirala

et al. 2012

Physica Status Solidi (b)

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“…Huang et al once reported that CF 2 Br 2 (17) reacted with terminal alkenes, styrene, diallyl ether, cyclohexene, a-pinene, b-pinene and cyclic enol ethers in an aqueous acetonitrile solution at room temperature or with cooling by an ice bath in the presence of Na 2 S 2 O 4 , sodium hydroxymethylsulfinate or thiourea dioxide, affording the corresponding adducts in good yields. Treatment of CF 2 Br 2 with alkynes in the presence of Na 2 S 2 O 4 gave the addition products as E-and Z-mixtures in moderate yields.…”

Section: Scope and Limitations Of The Standard Sulfinatodehalogenatio...mentioning

confidence: 99%

“…A mild two-step synthesis of polyfluoroalkanesulfonyl chlorides (57) starting from I(CF 2 ) 4 I was developed based on the sulfinatodehalogenation reaction (Scheme 11). 17 Treatment of I(CF 2 ) 4 I with 54 in the presence of AIBN furnished polyfluoroalkyl iodide as the starting material. Polyfluoroalkyl iodides 55 then reacted with Na 2 S 2 O 4 affording sodium perfluoroalkanesulfinate salts 56 which were converted into polyfluoroalkanesulfonyl chlorides 57 with N-chlorosuccinimide.…”

Section: Scope and Limitations Of The Standard Sulfinatodehalogenatio...mentioning

confidence: 99%

Progress in fluoroalkylation of organic compounds via sulfinatodehalogenation initiation system

et al. 2012

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The sulfinatodehalogenation reaction represents one of the most important methodologies to incorporate fluorine into organic molecules. Using inexpensive sulfur-containing reactants such as Na(2)S(2)O(4) under mild conditions, per- and polyfluoroalkyl halides (R(F)X, X = Br, I, CCl(3)) can be transformed smoothly into the corresponding sulfinate salts. This method is also used for the perfluoroalkylation of alkenes, dienes, alkynes and aromatics. Notably, after 1998, the sulfinatodehalogenation of perfluoroalkyl chlorides (R(F)Cl) has been realized by using dimethylsulfoxide (DMSO) as a solvent instead of CH(3)CN/H(2)O in the Na(2)S(2)O(4)/NaHCO(3) initiation system. Perfluoroalkyl chlorides, ethyl chlorofluoroacetates and chlorodifluoroacetates, and even nonfluorinated compounds, such as ethyl chloro- or dichloroacetates and chloroform, were either converted into the corresponding sulfinate salts or alkylated alkenes, alkynes and aromatics (including porphyrins). The sulfinatodehalogenation reaction has remarkable advantages. With the increasing demands to utilize the unique properties of fluorine and fluorinated functional groups in medicinal, agricultural and material sciences, we believe that there will continue to be useful developments in sulfinatodehalogenation chemistry and it will be applied more widely in the future.

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“…Industrially, per- and polyfluorinated surfactants were synthesized mainly by electrochemical fluorination (ECF) or oxidation of either fluorotelomer alcohols (FTOHs) or fluorotelomer sulfonyl chlorides (FTSCls). Both classes can be generated either by hydrolysis or the reaction of Na 2 S 2 O 4 and N -Chlorosuccinimide (NCS) with the respective fluorotelomer halogens (FTHals) [ 9 ]. In contrast to the previous mentioned methods, perfluorinated alkyl acids and carboxylates were mainly produced by the oxidation and hydrolysis of perfluoroalkyl iodides ( Figure 1 ).…”

Section: Introductionmentioning

confidence: 99%

“…chlorides (FTSCls). Both classes can be generated either by hydrolysis or the reaction of Na2S2O4 and N-Chlorosuccinimide (NCS) with the respective fluorotelomer halogens (FTHals) [9]. In contrast to the previous mentioned methods, perfluorinated alkyl acids and carboxylates were mainly produced by the oxidation and hydrolysis of perfluoroalkyl iodides (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Reductive Defluorination and Mechanochemical Decomposition of Per- and Polyfluoroalkyl Substances (PFASs): From Present Knowledge to Future Remediation Concepts

Roesch

Vogel

Simon

2020

IJERPH

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Over the past two decades, per- and polyfluoroalkyl substances (PFASs) have emerged as worldwide environmental contaminants, calling out for sophisticated treatment, decomposition and remediation strategies. In order to mineralize PFAS pollutants, the incineration of contaminated material is a state-of-the-art process, but more cost-effective and sustainable technologies are inevitable for the future. Within this review, various methods for the reductive defluorination of PFASs were inspected. In addition to this, the role of mechanochemistry is highlighted with regard to its major potential in reductive defluorination reactions and degradation of pollutants. In order to get a comprehensive understanding of the involved reactions, their mechanistic pathways are pointed out. Comparisons between existing PFAS decomposition reactions and reductive approaches are discussed in detail, regarding their applicability in possible remediation processes. This article provides a solid overview of the most recent research methods and offers guidelines for future research directions.

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A general method for the preparation of perfluoroalkanesulfonyl chlorides

Cited by 7 publications

References 15 publications

Manufacture and characterisation of thin flat and curved auxetic foam sheets

Manufacture and characterisation of thin flat and curved auxetic foam sheets

Progress in fluoroalkylation of organic compounds via sulfinatodehalogenation initiation system

Reductive Defluorination and Mechanochemical Decomposition of Per- and Polyfluoroalkyl Substances (PFASs): From Present Knowledge to Future Remediation Concepts

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