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The mechanism of electrophilic fluorination remains controversial. At issue is whether the reaction proceeds via an S N 2 or single-electron transfer (SET) process. In support of the S N 2 mechanism, aryl Grignard reagents and aryllithiums give similar yields of fluorobenzene in combination with N-fluoro-o-benzenedisulfonimide (NFOBS), even though the tendencies of these reagents to ...
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.
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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
As mentioned above, aryl and alkenyl nonaflates are useful as electrophiles in palladium catalyzed cross coupling reactions. Their reactivity generally mirrors that of the more commonly encountered triflate electrophiles, but nonaflates tend to be less prone to hydrolysis to ketones (in the case of alkenyl sulfonates) and phenols (in the case of aryl sulfonates).
Reductive fluorination: 2 CrO 2 F 2 + XeF 2 → 2 CrOF 3 + Xe +O 2. Aromatic fluorination: 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 ...
The electrophilic Br-Br molecule interacts with electron-rich alkene molecule to form a π-complex 1. Forming of a three-membered bromonium ion The alkene is working as an electron donor and bromine as an electrophile. The three-membered bromonium ion 2 consisted of two carbon atoms and a bromine atom forms with a release of Br −.
The species KHF 2 is relatively low melting, a good electrolyte, and an effective source of fluorine. The technology is sometimes called “CAVE” for Carbon Anode Vapor Phase Electrochemical Fluorination and was widely used at manufacturing sites of the 3M Corporation. The organic compound is fed through a porous anode leading to exchange of ...