56744-05-9Relevant academic research and scientific papers
Fluorination of Bi- and polycyclic aromatic hydrocarbons with N-fluorobis(phenylsulfonyl)amine in the absence of solvent
Borodkin,Elanov,Shubin
experimental part, p. 1317 - 1322 (2011/01/04)
Reactions of N-fluorobis(phenylsulfonyl)amine with naphthalene, 1-methylnaphthalene, phenanthrene, anthracene, and pyrene without solvent were investigated. Sometimes the fluorination of aromatic compounds with N-fluorobis(phenylsulfonyl)amine without solvent proceeded more selectively than at the use of fluorinating reagents in solution.
Facile one-pot fluorination of polycyclic aromatic hydrocarbons (PAHs) with N-fluoro-2,4-dinitroimidazole; scope and limitation
Laali, Kenneth K.,Tanaka, Mutsuo,Forohar, Farhad,Cheng, Michael,Fetzer, John C.
, p. 185 - 190 (2007/10/03)
The synthetic utility of N-fluoro-2,4-dinitro-imidazole NF-2,4-DNT, a recently introduced NF fluorinating agent, has been tested for direct one-pot fluorination of several classes of polycyclic aromatic hydrocarbons, PAHs, namely pyrene, crowded alkyl(cycloalkyl)-pyrenes; hexahydro-and tetrahydro-pyrene; benzo[a]anthracene; benzo[a]-and benzo[e] pyrene; perylene; 2,7-di-tert-butylphenanthrene;chrysene; 9-imethylanthracene and anthracene, as well as trans-15:16-dimethyl-dihydropyrene: azulene[2-a]lacenaphthylene and azulene. Although the isolated yields are modest, the ease of handling of the reagent, simple operation (reflux in dichloroethane for 3 days) and the use of 1.1 equivalent of the reagent makes the procedure quite attractive for polynuclear aromatics, avoiding multi-step operations (NO2-PAH → NH2-PAH → N2+-PAH → F-PAH) or the use of toxic or costly reagents (CF3OF, XeF2, etc.); it provides direct one-pot access to a variety of F-PAHs that are not readily made using: other fluorinating agents.
Selective and efficient direct fluorination of polycyclic aromatic hydrocarbons using 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)
Stavber, Stojan,Zupan, Marko
, p. 1077 - 1078 (2007/10/03)
A new N-F fluorinating reagent 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Accufluor NFTh) was effectively used for selective fluorination of polycyclic aromatics. Naphthalene was site-selectively fluorinated to 1-fluoronaphthalene, phenanthrene to 9-fluorophenanthrene, and pyrene to 1-fluoropyrene. In a series of substituted naphthalenes the regioselectivity and effectiveness of fluorination depended on the position and the nature of the substituents.
Fluorination of Polycyclic Aromatic Hydrocarbons: Charge vs. Frontier Orbital Control in Substitution Reactions of Radical Cations
King, Patrick F.,O'Malley, Robert F.
, p. 2803 - 2807 (2007/10/02)
The anodic fluorination of perylene and pyrene in acetonitrile occurred at potentials consistent with the intermediacy of dications, but that of triphenylene with its radical cation.Fluorination of anthracene compounds at a meso position occurred by the a
ROOM TEMPERATURE FLUORINATION OF AROMATIC MOLECULES WITH CESIUM FLUOROXYSULPHATE
Stavber, Stojan,Zupan, Marko
, p. 597 - 600 (2007/10/02)
Room-temperature fluorination of benzene with cesium fluoroxysulphate in the presence of boron trifluoride as catalyst resulted in the formation of fluorobenzene, while reaction with naphthalene gave 1-fluoro and 2-fluoronaphthalene in the ratio 5:1, the overall yield being between 38 and 42percent.The fluorination of phenanthrene and pyrene should be carried out at higher dilution and needs no catalyst.Phenanthrene gave 9-fluorophenanthrene and 9,9-difluoro-10-keto-9,10-dihydrophenanthrene in the ratio 1:6 in a yield of about 70percent, while pyrene gave 1-fluoro and 4-fluoropyrene in the ratio 7.5:1.
