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Radical fluorination is a type of fluorination reaction, complementary to nucleophilic and electrophilic approaches. [1] It involves the reaction of an independently generated carbon-centered radical with an atomic fluorine source and yields an organofluorine compound .
Organofluorine compounds are prepared by numerous routes, depending on the degree and regiochemistry of fluorination sought and the nature of the precursors. The direct fluorination of hydrocarbons with F 2, often diluted with N 2, is useful for highly fluorinated compounds: R 3 CH + F 2 → R 3 CF + HF
In reductive hydrodefluorination the fluorocarbon is reduced in a series of single electron transfer steps through the radical anion, the radical and the anion with ultimate loss of a fluorine anion. An example is the conversion of pentafluorobenzoic acid to 3,4,5-tetrafluorobenzoic acid in a reaction of zinc dust in aqueous ammonia.
In contrast, the fluoropolymers are formed by polymerizing free radicals; other techniques used for hydrocarbon polymers do not work in that way with fluorine. [118] The range of organofluorine compounds is diverse, reflecting the inherent complexity of organic chemistry. A vast number of small molecules exist with varying amounts of fluorine ...
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In organic chemistry, free-radical halogenation is a type of halogenation. This chemical reaction is typical of alkanes and alkyl-substituted aromatics under application of UV light. The reaction is used for the industrial synthesis of chloroform (CHCl 3), dichloromethane (CH 2 Cl 2), and hexachlorobutadiene. It proceeds by a free-radical chain ...
Structure of [(C 5 Me 5) 2 Ti(FC 6 H 5)] +, a coordination complex of fluorobenzene.. PhF is a useful solvent for highly reactive species. Its melting point at -44 °C is lower than that of benzene.
A free radical is formed from the carboxylic acid in an oxidative decarboxylation with silver salts and an oxidizing agent. The oxidizing agent (ammonium persulfate) oxidizes the Ag(+) to Ag(2+) under the acidic reaction conditions. This induces a hydrogen atom abstraction by the silver, followed by radical decarboxylation.