N-halogeno compounds. Part 12 [1]. Site-specific fluorination of carbanions with perfluoro-N-fluoropiperidine [2]

Banks, R. E.; Murtagh, Vincent; Tsiliopoulos, E.

doi:10.1016/s0022-1139(00)80353-x

Cited by 45 publications

(9 citation statements)

References 23 publications

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“…The reagent 1 is effective in fluorination of aryl anions, the Grignard reagents, 2-nitropropane sodium salt, diethyl malonate derivatives, etc. 21,22 Ph 3 PF 2 was obtained in the reaction with triphenylphosphine. 23 Phenols and N,N-dialkylanilines are fluorinated with the reagent 1 to give a mixture of ortho-and para-fluoro derivatives.…”

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 a previous research aimed at synthesizing some regioselectively fluorinated profens, we found that 2-aryl-2-fluoropropionic acid can be easily obtained from the corresponding 2-hydroxyesters by DAST-promoted OH/F permutation followed by alkaline hydrolysis of the resulting 2-fluoroester [22]. At the same time, we noticed that dialkyl 2-alkyl-2-fluoromalonates were prepared by exhaustive alcoholysis of hexafluoropropene followed by base-promoted alkylation of the resulting 2-fluoromalonates with alkyl halogenides [23] or, alternatively, by fluorination of dialkyl 2-alkylsodiomalonates with either Xenon difluoride [24] or electrophilic NF fluorinating reagents [25][26][27]. However, direct DAST-promoted fluorination of dialkyl 2-alkyl-2-hydroxymalonates was never reported.…”

Section: Introductionmentioning

confidence: 93%

Are carboxylic esters really refractory to DAST? On the fluorination of α-hydroxyesters with DAST

Lepri

Buonerba

Maccaroni

et al. 2015

Journal of Fluorine Chemistry

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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%

“…Another noteworthy issue is the reaction mechanism for the fluorination with N -F reagents. There have been long standing arguments regarding which mechanism is operating in these fluorinations: a single-electron transfer (SET) or a nucleophilic substitution (S N 2) mechanism ( Scheme 100 ) [ 22 , 142 ]. In the SET process, a single-electron transfer from a substrate (Nu − ) to a N -F reagent [N-F] occurs to form a radical anion [N-F] · − and a Nu · radical, and the former undertakes the homolytic N–F bond cleavage to give a F · radical and a N: − anion, and then the F · radical and the Nu · radical combine to generate the final product Nu–F.…”

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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N-halogeno compounds. Part 12 [1]. Site-specific fluorination of carbanions with perfluoro-N-fluoropiperidine [2]

Cited by 45 publications

References 23 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

Are carboxylic esters really refractory to DAST? On the fluorination of α-hydroxyesters with DAST

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

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