Search results
Results from the WOW.Com Content Network
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 .
Radical fluorination with the pure element is difficult to control and highly exothermic; care must be taken to prevent an explosion or a runaway reaction. With chlorine the reaction is moderate to fast; with bromine, slow and requires intense UV irradiation ; and with iodine, it is practically nonexistent and thermodynamically unfavored.
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
The reaction typically involves free radical pathways. The regiochemistry of the halogenation of alkanes is largely determined by the relative weakness of the C–H bonds. This trend is reflected by the faster reaction at tertiary and secondary positions. Free radical chlorination is used for the industrial production of some solvents: [2]
Trifluoromethyl hypofluorite is an organofluorine compound with the chemical formula C F 3 OF.It exists as a colorless gas at room temperature and is highly toxic. [1] It is a rare example of a hypofluorite (compound with an O−F bond).
Alkene fluorination: Radical fluorination in radical decarboxylative fluorination reactions, [ 10 ] in Hunsdiecker-type reactions where xenon difluoride is used to generate the radical intermediate as well as the fluorine transfer source, [ 28 ] and in generating aryl radicals from aryl silanes: [ 29 ]
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 ...
Electrophilic fluorinating reagents could in principle operate by electron transfer pathways or an S N 2 attack at fluorine. This distinction has not been decided. [2] By using a charge-spin separated probe, [3] it was possible to show that the electrophilic fluorination of stilbenes with Selectfluor proceeds through an SET/fluorine atom transfer mechanism.