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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.
Joseph H. Simons (10 May 1897 – 30 December 1983) was a U.S. chemist who became famous for discovering one of the first practical ways to mass-produce fluorocarbons in the 1930s while a professor of chemical engineering at Pennsylvania State University.
Electrochemical fluorination (ECF), or electrofluorination, is a foundational organofluorine chemistry method for the preparation of fluorocarbon-based organofluorine compounds. [1] The general approach represents an application of electrosynthesis .
Starting in the late 1940s, a series of electrophilic fluorinating methodologies were introduced, beginning with CoF 3. Electrochemical fluorination ("electrofluorination") was announced, which Joseph H. Simons had developed in the 1930s to generate highly stable perfluorinated materials compatible with uranium hexafluoride. [15]
He conducted research on the chemistry of [C-F-C] fluoronium ions [16] and later reported first spectroscopic evidence for fluoronium ions in a solution. [17] Lectka has also worked on metal-catalyzed aliphatic fluorination [ 18 ] and site-selective aliphatic fluorination.
The lithium enolates of methyl ketones give mixtures of products derived from electrophilic attack on the O (expected) or C (unexpected) atoms of the enolate. This effect is particularly evident with the lithium enolate of pinacolone, which gives a 2:1 mixture favoring C-attack.
More recently, trifluoromethylation of diazonium salts has been developed and is referred to as a 'Sandmeyer-type' reaction. Diazonium salts also react with boronates, iodide, thiols, water, hypophosphorous acid and others, [6] and fluorination can be carried out using tetrafluoroborate anions (Balz–Schiemann reaction). However, since these ...
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