Polymeric analogues of electrophilic fluorinating agents of the N-F class

Banks, R. E.; Tsiliopoulos, E.

doi:10.1016/s0022-1139(00)85081-2

Cited by 13 publications

(12 citation statements)

References 15 publications

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“…It is assumed that this reaction gives rise to the stable phenoxyl radical 5. 27 Polyfluorinated polyethylene 6 containing perfluoropiperidine rings with the N7F bond as substituents also possesses the properties of a fluorinating reagent. 27 Fluorination of sodium diethyl phenylmalonate with the reagent 6 has been described.…”

Section: The Use Of Perfluoro-n-fluoropiperidinementioning

confidence: 99%

N-Fluoro amines and their analogues as fluorinating reagents in organic synthesis

Fürin¹,

Fainzil'berg²

1999

Russ. Chem. Rev.

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We show that adiabatic, super-Hubble, and almost scale invariant density fluctuations are produced by cosmic strings in a contracting universe. An essential point is that isocurvature perturbations produced by topological defects such as cosmic strings on super-Hubble scales lead to a source term which seeds the growth of curvature fluctuations on these scales. Once the symmetry has been restored at high temperatures, the isocurvature seeds disappear, and the fluctuations evolve as adiabatic ones in the expanding phase. Thus, cosmic strings may be resurrected as a mechanism for generating the primordial density fluctuations observed today.

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Section: The Use Of Perfluoro-n-fluoropiperidinementioning

confidence: 99%

N-Fluoro amines and their analogues as fluorinating reagents in organic synthesis

Fürin¹,

Fainzil'berg²

1999

Russ. Chem. Rev.

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“…In their example, the authors initially brominated and then lithiated linear polystyrene. The lithiated polystyrene was then reacted with PFPy to yield 6 ( Scheme 10 ) [ 60 ]. Polymer 6 was fully fluorinated by treatment with F 2 /N 2 .…”

Section: Perfluoropyridine Used In Polymers and Materialsmentioning

confidence: 99%

“…Table 2 summarizes the data collected for 2 and 3 [56]. About 10 years later, the next known study of using PFPy in a polymer was reported by Banks and Tsilliopoulos [60]. In their example, the authors initially brominated and then lithiated linear polystyrene.…”

Section: Perfluoropyridine Used In Polymers and Materialsmentioning

confidence: 99%

Perfluoropyridine: Discovery, Chemistry, and Applications in Polymers and Material Science

et al. 2022

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Perfluoropyridine (PFPy) is an organofluorine compound that has been employed for a variety of applications, from straightforward chemical synthesis to more advanced functions, such as fluorinated networks and polymers. This can be directly attributed to the highly reactive nature of PFPy, especially towards nucleophilic aromatic substitution (SNAr). The aim of this review is to highlight the discovery and synthesis of PFPy, discuss its reactive nature towards SNAr, and to summarize known reports of the utilization and thermal analysis of PFPy containing fluoropolymers and fluorinated network materials.

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“…In 1986, Banks and co-worker reported the preparation of polymeric analogues of perfluoro- N -fluoropiperidine ( 1-1 ) [ 21 ] and then in 1991, Banks et al reported the improved yields of the reactions of 1-1 with sodium salts of 2-nitropropane, malonate esters, and a keto ester, and phenylmagnesium bromide [ 22 ]. However, the fluorinated products were still accompanied by considerable amounts of byproducts resulting from the reaction of the substrates with 1-5 .…”

Section: Reviewmentioning

confidence: 99%

Development of N-F fluorinating agents and their fluorinations: Historical perspective

Umemoto¹,

Yang²,

Hammond³

2021

Beilstein J. Org. Chem.

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This review deals with the historical development of all N-F fluorinating agents developed so far. The unique properties of fluorine make fluorinated organic compounds attractive in many research areas and therefore fluorinating agents are important. N-F agents have proven useful by virtue of their easy handling. This reagent class includes many types of N-F compounds: perfluoro-N-fluoropiperidine, N-fluoro-2-pyridone, N-fluoro-N-alkylarenesulfonamides, N-fluoropyridinium salts and derivatives, N-fluoroquinuclidium salts, N-fluoro-trifluoromethanesulfonimide, N-fluoro-sultams, N-fluoro-benzothiazole dioxides, N-fluoro-lactams, N-fluoro-o-benzenedisulfonimide, N-fluoro-benzenesulfonimide, 1-alkyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts, N-fluoropyridinium-2-sulfonate derivatives, 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane salts, N-fluorodinitroimidazole, N-fluoro-trichloro-1,3,5-triazinium salt, N-F ethano-Tröger’s base derivatives, N-fluoro-methanesulfonimide, N-fluoro-N-arylarenesulfonamides, bisN-F salts such as N,N’-difluorobipyridinium salts and N,N’-difluoro-1,4-diazoniabicyclo[2.2.2]octane salts, and their many derivatives and analogs, including chiral N-F reagents such as optically active N-fluoro-sultam derivatives, N-fluoro-alkaloid derivatives, DABCO-based N-F derivatives, and N-F binaphthyldisulfonimides. The synthesis and reactions of these reagents are described chronologically and the review also discusses the relative fluorination power of each reagent and their mechanisms chronicling developments from a historical perspective.

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Polymeric analogues of electrophilic fluorinating agents of the N-F class

Cited by 13 publications

References 15 publications

N-Fluoro amines and their analogues as fluorinating reagents in organic synthesis

N-Fluoro amines and their analogues as fluorinating reagents in organic synthesis

Perfluoropyridine: Discovery, Chemistry, and Applications in Polymers and Material Science

Development of N-F fluorinating agents and their fluorinations: Historical perspective

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