N-halogeno compounds. Part 9. N-Fluoroquinuclidinium fluoride—a new electrophilic fluorinating agent

Banks, R. E.; Boisson, R. A. Du; Morton, William D.; Tsiliopoulos, E.

doi:10.1039/p19880002805

Cited by 38 publications

(16 citation statements)

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“…132, 169 ± 176 Fluoroquinuclidinium fluoride (81a) was obtained in 83% ± 89% yield by direct fluorination of quinuclidine with 10% F 2 in CFCl 3 at 778 8C. 169,171,175,176 Later, preparation of N-fluoroquinuclidinium salts with other counterions was performed by fluorination of quinuclidine in the presence of the corresponding salts (the Umemoto method). With LiOTf, N-fluoroquinuclidinium triflate (81b) was obtained in 88% yield (fluorination in MeCN at 733 8C).…”

Section: N-fluoroquinuclidinium and 4-alkyl-1-fluoro-14diazoniabicycl...mentioning

confidence: 99%

“…The synthesis of the reagent 90 could be carried out by fluorination of 1,4diazabicyclo[2.2.2]octane with elemental fluorine in acetonitrile in the presence of BF 3 and PF 5 or in acetone in the presence of BF 3 . 169 Later, polyfluorinated alcohols [e.g., (CF 3 ) 2 CHOH)] and sulfuric acid were used as fluorination media (yield > 80%). Yet another convenient approach to the synthesis of the reagent 90 is the fluorination of the trimethylsilyl derivative 91.…”

Section: N-fluoroquinuclidinium and 4-alkyl-1-fluoro-14diazoniabicycl...mentioning

confidence: 99%

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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: N-fluoroquinuclidinium and 4-alkyl-1-fluoro-14diazoniabicycl...mentioning

confidence: 99%

Section: N-fluoroquinuclidinium and 4-alkyl-1-fluoro-14diazoniabicycl...mentioning

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 1986 as the N -F pyridinium reagents were emerging, Banks et al disclosed the quaternary ammonium N -F reagent, N -fluoroquinuclidinium fluoride ( 6-1 ) [ 43 ]. They subsequently followed with more detailed results in 1988 [ 44 ]. Quinuclidine was fluorinated by neat fluorine in trichlorofluoromethane at −72 °C, affording the product 6-1 in 86% yield ( Scheme 15 ).…”

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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“…Several novel N-fluoroqulnuclidinium salts have been synthesized recently (Banks, Du Boisson, Morton & Tsiliopoulos, 1988;Banks & Sharif, 1991) as part of the continuing search for safe, easily handled, non-gaseous electrophilic fluorinating agents for use in organic synthesis. The title molecule (I) was prepared in order to determine if changes occur in the quinuclidine moiety on lonepair donation to a typical Lewis acid.…”

Section: Commentmentioning

confidence: 99%

“…The tide molecule, including atomic numbering scheme; drawn synthesized recently (Banks, Du Boisson, Morton & using ORTEPII (Johnson, 1976). Tsiliopoulos, 1988;Banks & Sharif, 1991) as part of the continuing search for safe, easily handled, non-gaseous electrophilic fluorinating agents for use in organic synthesis (Furin, 1989). In connection with mechanistic studies of the mode of action of these salts, and the stereochemistry involved (Banks, Mohialdin-Khaffaf & Sharif, …”

mentioning

confidence: 99%

Quinuclidine-trifluoromonoborane: a (1/1) Lewis base-Lewis acid complex

Banks¹,

Besheesh²,

Pritchard³

et al. 1993

Acta Crystallogr C

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N-halogeno compounds. Part 9. N-Fluoroquinuclidinium fluoride—a new electrophilic fluorinating agent

Cited by 38 publications

References 1 publication

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

Quinuclidine-trifluoromonoborane: a (1/1) Lewis base-Lewis acid complex

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