Elemental fluorine

Chambers, Richard D.; Joel, Andrew K.; Rees, Anthony J.

doi:10.1016/s0022-1139(99)00218-3

Cited by 25 publications

(9 citation statements)

References 12 publications

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“…Partially fluorinated substrates are excellent starting materials for perfluorination because the presence of fluorine atoms in an organic molecule lowers the oxidation potential of the system, thereby enhancing the stability of the substrate towards the sometimes necessarily harsh perfluorination conditions [8,24]. Furthermore, the fluorinated groups render the substrate more soluble in the fluorinated solvents that are often used for such reactions.…”

Section: Perfluorinationmentioning

confidence: 99%

“…Furthermore, the fluorinated groups render the substrate more soluble in the fluorinated solvents that are often used for such reactions. Using this strategy, perfluorination of a range of ethers and polyethers bearing hexafluoropropyl units has been achieved (Scheme 3) [24]. The use of small molecular weight polyfluoroethers 1, which are themselves perfluorinated under the reaction conditions, as a solvent for perfluorination of high molecular weight polyether derivatives allows perfluorination reactions to be carried out in non-ozone depleting solvents.…”

Section: Perfluorinationmentioning

confidence: 99%

See 1 more Smart Citation

Elemental fluorine in organic chemistry (1997–2006)

Sandford

2007

Journal of Fluorine Chemistry

125

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Section: Perfluorinationmentioning

confidence: 99%

Section: Perfluorinationmentioning

confidence: 99%

Elemental fluorine in organic chemistry (1997–2006)

Sandford

2007

Journal of Fluorine Chemistry

125

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“…This is in contrast to the solubility of a non-fluorinated compound. [11] As described in the literature [6,11b] , the appropriate dilution of fluorine, the appropriate dilution of the substrate in an inert solvent, and use of an excess amount of fluorine to replace all of the hydrogen atoms in the substrate at all times are essential. In order to achieve this, the continuous feed of both diluted fluorine gas and the substrate in perfluorinated solvent at a controlled rate with a molar ratio F 2 /H = 2.8 was carried out.…”

Section: Resultsmentioning

confidence: 99%

A New Route to Perfluoro(Propyl Vinyl Ether) Monomer: Synthesis of Perfluoro(2-propoxypropionyl) Fluoride from Non-Fluorinated Compounds

et al. 2001

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Perfluoro(2‐propoxypropionyl) fluoride (1a), which is the precursor of the perfluorinated propyl vinyl ether (PPVE) monomer of an industrially important perfluoroalkoxy copolymer (PFA), was synthesized by utilizing direct fluorination of the non‐fluorinated counterpart for the first time. The partially‐fluorinated ester 7 synthesized from the desired perfluorinated acid fluoride 1a itself and the non‐fluorinated alcohol 5, which has a carbon skeleton corresponding to the desired compound 1a, was perfluorinated by liquid‐phase direct fluorination with elemental fluorine. Degradation of the resulting perfluorinated ester 8 gave 2 mols of the desired acid fluoride 1a. In a sense, this process can be called self‐multiplication of a perfluorinated acid fluoride from a non‐fluorinated alcohol.

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“…These hydrofluoroethers (HFEs) have been described in several scientific contributions [1][2][3]. Different methods are available for their synthesis: (1) fluorination of ethers [4][5][6][7][8][9], (2) nucleophilic or radical addition to fluoroolefins [10][11][12], (3) electrophilic alkylation of appropriate fluorinated substrates [13][14][15][16], (4) decarboxylation of fluorinated substrates in presence of hydrogen donors [3], and, finally, (5) reaction of perfluoropolyether diacyl fluorides with methyl fluoroformate [17].…”

Section: Introductionmentioning

confidence: 99%