Fluorinated Aromatic Compounds

Abstract

This article covers the preparation, properties, reactions, and applications of three types of fluorinated aromatic compounds: ring‐fluorinated aromatics, side‐chain fluorinated aromatics and arylfluoroalkyl ethers, and fluorinated nitrogen heterocyclics. The special properties conferred by fluorine justify the higher costs required to produce fluoroaromatics. Depending on which substituents are present, fluoroaromatic intermediates can be converted into fluorinated or fluorine‐free commercial end products. Fluorine‐containing aromatics have been incorporated into drugs (hypnotics, tranquilizers, antiinflammatory agents, analgesics, antibacterials) and into crop‐protection chemicals (herbicides, insecticides, fungicides). Liquid crystals, positron emission tomography, and imaging systems represent new areas where fluoroaromatics and fluoroheterocyclics have gained attention. For fluorine‐free end products, the lability of fluorine in fluoronitrobenzenes and other activated molecules permit it to serve as a handle in hair dye manufacturing operations, high performance polymers (eg, PEEK), drugs (eg, diuretics), fiber‐reactive dyes, analytical applications, and biological diagnostic reagents.

Perfluorocycloparaphenylenes: Fully fluorinated carbon nanorings by Ni-mediated one-pot synthesis

“…Owing to its negative inductive effect, the incorporation of fluorine into materials leads to a decrease in orbital energy. As such, it is important to develop synthetic methods that provide access to aromatic molecules containing many C-F bonds [7][8][9] , and the extreme targets of the research field are aromatic molecules wherein all hydrogen atoms are replaced with fluorine atoms, i.e., perfluoroarenes [10][11][12][13][14] . However, methods to synthesize strained perfluoroarenes remain very limited.…”

Dissociative electron attachment to fluorinated nitrobenzenes

“…for radiosensitizing agents, and to enhance the impact of crop protecting chemicals [3][4][5]. Difluorobenzenes are relevant intermediates for the production of herbicides, fungicides and insecticides and trifluoronitrobenzene, for example, can be used in the synthesis of fluoroquinolone antibacterials such as ofloxacin [6].…”

Kinetics of the Reaction of 2‐Chloro‐3,5‐dinitrobenzotriflouride with Aniline in Toluene and Methanol‐Toluene Mixed Solvents

“…[1][2][3] Fluorine-containing aromatics have been incorporated into drugs (hypnotics, tranquilizers, anti-inflammatory agents and analgesics, antibacterial) and into crop-protection chemicals (herbicides, insecticides, fungicides). [4] Aryl halides are common substrates to react with nucleophilic aromatic substitution. In recent years, the photo dissociation dynamics of aryl halides has been a subject of intensive studies, which is closely related to the atmospheric chemistry.…”