A new synthetic approach to poly- and perfluorinated polyethers

Hung, Ming; Farnham, William B.; Feiring, Andrew E.; Rozen, Shlomo

doi:10.1021/ja00073a009

Cited by 46 publications

(37 citation statements)

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“…Regarding the decomposition of the dioxolane ring, Hung has reported similar phenomena during synthesis of PDD [12]. The estimated cleavage of the C-O bond of dioxolane supports the possibility of Scheme 4, even though the position of the anion of each intermediate was different.…”

Section: Resultssupporting

confidence: 54%

Synthesis and polymerization of a novel perfluorinated monomer

Murotani

Saitō

Sawaguchi

et al. 2007

Journal of Fluorine Chemistry

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Section: Resultssupporting

confidence: 54%

Synthesis and polymerization of a novel perfluorinated monomer

Murotani

Saitō

Sawaguchi

et al. 2007

Journal of Fluorine Chemistry

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“…A tricyclic ring/cage system of RC 6 H 5 ·5BNR' 2 products were formed by reactions between dehalogenation products of F 2 BN( i -Pr) 2 with monoalkylbenzenes using monoglyme as the co-solvent. 274 Hung et al 275 prepared linear and cyclic perfluorinated polyethers through the ionic polymerization of a trifluorovinyl ether alcohol (CF 2 =CFOR f CH 2 OH, R f = CF 2 CF(CF 3 )OCF 2 CF 2 ) and the subsequent fluorination of the polyfluorinated polyethers (Scheme 32). They found that without a solvent, linear polymers with M n values up to 29,000 were produced, while in glyme solution, cyclic oligomers were major products and a cyclic dimer was obtained in yields up to 60%.…”

Section: Uses In Organic Reactionsmentioning

confidence: 99%

Glymes as versatile solvents for chemical reactions and processes: from the laboratory to industry

2014

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Glymes, also known as glycol diethers, are saturated non-cyclic polyethers containing no other functional groups. Most glymes are usually less volatile and less toxic than common laboratory organic solvents; in this context, they are more environmentally benign solvents. However, it is also important to point out that some glymes could cause long-term reproductive and developmental damages despite their low acute toxicities. Glymes have both hydrophilic and hydrophobic characters that common organic solvents are lack of. In addition, they are usually thermally and chemically stable, and can even form complexes with ions. Therefore, glymes are found in a broad range of laboratory applications including organic synthesis, electrochemistry, biocatalysis, materials, and Chemical Vapor Deposition (CVD), etc. In addition, glyme are used in numerous industrial applications, such as cleaning products, inks, adhesives and coatings, batteries and electronics, absorption refrigeration and heat pumps, as well as pharmaceutical formulations, etc. However, there is a lack of comprehensive and critical review on this attractive subject. This review aims to accomplish this task by providing an in-depth understanding of glymes’ physicochemical properties, toxicity and major applications.

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“…However, they do coordinate anions, such as O 2 À and F À , in the gas phase [46]. Synthetic routes circumventing the direct fluorination step were developed by Scheme 9. researchers at DuPont, who obtained poly-and perfluorinated polyethers with oxygen atoms directly linked to -CF 2 -units, which were still devoid of any complexation ability towards metal cations [47,48].…”

Section: Fluorous Crown Ethersmentioning

confidence: 99%