N-halogeno compounds. Part 16. Perfluoro-[N-fluoro-N-(4-pyridyl)acetamide] — a new site-selective electrophilic fluorinating agent

Banks, R. E.; Besheesh, Mohamed K.; Tsiliopoulos, E.

doi:10.1016/0022-1139(95)03380-7

Cited by 14 publications

(10 citation statements)

References 15 publications

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“…32 ± 34 The reagent 8 fluorinates diethyl phenylmalonate (NaH, THF, from 710 to 20 8C) to give the fluoro derivative 6 in 66% yield. 32 The reaction with enamines results in the corresponding afluoro ketones. 32 The reactions with phenol (MeOH, 20 8C) and anisole (MeCN, 20 8C) yield mixtures of ortho-and para-isomers (in 1 : 1 and 7 : 3 ratios, respectively).…”

Section: The Use Of N-fluoro-2-pyridonementioning

confidence: 99%

“…32 The reaction with enamines results in the corresponding afluoro ketones. 32 The reactions with phenol (MeOH, 20 8C) and anisole (MeCN, 20 8C) yield mixtures of ortho-and para-isomers (in 1 : 1 and 7 : 3 ratios, respectively). 32 Fluorination of sulfonamides with F 2 in the presence of KF or with a FClO 3 ± NaH mixture gives the corresponding N-fluoro derivatives of the type 9 (yield * 60%).…”

Section: The Use Of N-fluoro-2-pyridonementioning

confidence: 99%

See 1 more Smart Citation

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 N-fluoro-2-pyridonementioning

confidence: 99%

Section: The Use Of N-fluoro-2-pyridonementioning

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 1996, the Banks group reported perfluoro[ N -fluoro- N -(4-pyridyl)acetamide] ( 21-3 ) as a carboxamide analogue of perfluoro[ N -fluoro- N -(4-pyridyl)methanesulfonamide] ( 11-2 , see section 1-11) [ 82 ]. Its precursor, 21-2 , was prepared from pentafluoropyridine by either one of two methods ( Scheme 46 ).…”

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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“…Typical procedure for the reaction of polyhalopyridines with liquid NH 3 Polyhalopyridine was placed into a steel autoclave, the required amount of liquid NH 3 was added through a measuring funnel with back pressure and the autoclave was sealed. The reaction mixture was heated up to the given temperature upon stirring by rotation Entries 2,5,6,7,[9][10][11] Purity of the crude products in Entries 1, 3, 5, 7-11 is >95%, in Entries 2, 4, 6 is >90% ( 19 F NMR data). c Preparation of compounds 1b, 2b and 4b has been reported in [1].…”

Section: Synthetic Proceduresmentioning

confidence: 99%

“…Monoamination of pyridines 1a-3a at the g-position, and pyridines 4a and 5a at the a-position is known to proceed selectively in aqueous NH 3 or in its mixtures with organic solvents (dioxane, THF) (1a [7], 2a [8], 3a [4], 4a [9], 5a [9,10]). Monoamination of pyridines 6a and 8a results in a mixture of isomers containing a-or g-amino group [11,12]; there are no data about ammonolysis of pyridine 7a.…”

Section: Introductionmentioning

confidence: 99%

Direct di- and triamination of polyfluoropyridines in anhydrous ammonia

Kusov¹,

Rodionov²,

Vaganova³

et al. 2009

Journal of Fluorine Chemistry

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N-halogeno compounds. Part 16. Perfluoro-[N-fluoro-N-(4-pyridyl)acetamide] — a new site-selective electrophilic fluorinating agent

Cited by 14 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

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

Direct di- and triamination of polyfluoropyridines in anhydrous ammonia

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