Rearrangements with Migration of a Fluorine Atom

Kobrina, L. S.; Kovtonyuk, V. N.

doi:10.1070/rc1988v057n01abeh003335

Cited by 22 publications

(28 citation statements)

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“…For instance, the reaction of the latter with piperidine at 17 °C leads to 5,8 difluoro 6 pi peridinoquinoline (27) and 5,6 difluoro 8 piperidino quinoline (28) in the ratio 1 : 4 (Scheme 6; see Table 1, entry 14), whereas in boiling piperidine, the products specified are formed in the ratio 1 : 9 (see Table 1, entry 15). A predominant isomer 28 was isolated and characterized as an individual compound.…”

Section: Methodsmentioning

confidence: 98%

Reaction of quinolines fluorinated at the benzene ring with nitrogen-centered nucleophiles

et al. 2009

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A primary functionalization of quinolines polyfluorinated at the benzene ring (5,7 difluoro , 5,7,8 trifluoro , 5,6,8 trifluoro , 8 chloro 5,7 difluoro , 5,6,7,8 tetrafluoro , and 5,7,8 trifluoro 6 (trifluoromethyl)quinolines) by the reaction with nitrogen centered nucleophiles (aqueous and liquid ammonia, hydrazine hydrate, piperidine) has been studied. If the molecule of fluorinated quinoline contains three or four halogen atoms, their combined orientation effect outweighs the influence of the heterocycle N atom. It was found that the orientation of substitution in the reactions of 5,6,8 trifluoro and 5,7,8 trifluoro 6 (trifluoromethyl)quinolines with piperidine depends on temperature, because the enthalpy control of the ratio of the rates of competing reactions changes to the entropy control. Nineteen new quinoline derivatives containing F atoms and amino or modified amino groups in the benzene ring have been obtained.

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Section: Methodsmentioning

confidence: 98%

Reaction of quinolines fluorinated at the benzene ring with nitrogen-centered nucleophiles

et al. 2009

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“…The lack of reaction with most electrophiles precludes the syntheses of phosphines by a route which is extremely convenient for non-fluorinated phosphines, such as dppe, which is prepared by the reaction between diphenylphosphide and 1,2-dichloroethane [87]. However, since fluoroaromatic compounds undergo S N Ar reactions [88], phosphines bearing only one fluoroaromatic substituent may be synthesized readily by the reaction between a polyfluoroaromatic compound and a nucleophilic phosphide, secondary phosphine or equivalent. The success of the synthesis is highly dependent on the nucleophilicity of the phosphorus reagent, the nature of the substrate and the temperature.…”

Section: Nucleophilic Phosphorusmentioning

confidence: 99%

“…The success of the synthesis is highly dependent on the nucleophilicity of the phosphorus reagent, the nature of the substrate and the temperature. Typically substitution occurs para to substituents [88], and this can be used to direct the positions of di-and poly-substitution, for example in the syntheses of chelating ortho-fluorophenylene bridged diphosphines [53].…”

Section: Nucleophilic Phosphorusmentioning

confidence: 99%

“…Fluoroarylphosphines are susceptible to nucleophilic attack [88], with substitution of the para-fluorine atoms observed in most cases. The susceptibility of polyfluoroaryl substituents to nucleophilic attack can be enhanced by coordination to metals, especially in cases where the resulting complex is cationic [128].…”

Section: Reactions Involving C-f Bond Cleavagementioning

confidence: 99%

“…The susceptibility of fluoroarenes to nucleophilic attack [88] offers an attractive route to their functionalization. However, the susceptibility of the P-C(ArF) bond to cleavage by nucleophiles can be problematic to the synthesis of the desired product.…”

Section: Functionalizationmentioning

confidence: 99%

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