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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.
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
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.
Example of a reduction–oxidation reaction between sodium and chlorine, with the OIL RIG mnemonic [1] Tetracyanoquinodimethane is an organic electron-acceptor. Electron acceptors participate in electron-transfer reactions. In this context, the oxidizing agent is called an electron acceptor and the reducing agent is called an electron donor.
Chlorine and oxygen can bond in a number of ways: chlorine monoxide radical, ClO•, chlorine (II) oxide radical; chloroperoxyl radical, ClOO•, chlorine (II) peroxide radical; chlorine dioxide, ClO 2, chlorine (IV) oxide; chlorine trioxide radical, ClO 3 •, chlorine (VI) oxide radical; chlorine tetroxide radical, ClO 4 •, chlorine (VII ...
Perchloryl fluoride is produced primarily by the fluorination of perchlorates. The initial syntheses in the early 1950s used fluorine gas or fluorides and anodic oxidation as the fluorinating agents, but these give explosive gaseous mixtures. [8] A common fluorinator in modern syntheses is antimony pentafluoride: [3]: 372–373 ClO − 4 + 3 HF ...
Such reagents include cobalt trifluoride, chlorine trifluoride, and iodine pentafluoride. [4] The method electrochemical fluorination is used commercially for the production of perfluorinated compounds. It generates small amounts of elemental fluorine in situ from hydrogen fluoride. The method avoids the hazards of handling fluorine gas.
A common preparative method involves fluorination of sodium hydroxide: 2 F 2 + 2 NaOH → OF 2 + 2 NaF + H 2 O. OF 2 is a colorless gas at room temperature and a yellow liquid below 128 K. Oxygen difluoride has an irritating odor and is poisonous. [3] It reacts quantitatively with aqueous haloacids to give free halogens: OF 2 + 4 HCl → 2 Cl 2 ...