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Fluorobenzene is an aryl fluoride and the simplest of the fluorobenzenes, with the formula C 6 H 5 F, often abbreviated PhF. A colorless liquid, it is a precursor to many fluorophenyl compounds. A colorless liquid, it is a precursor to many fluorophenyl compounds.
The Sandmeyer reaction is a chemical reaction used to synthesize aryl halides from aryl diazonium salts using copper salts as reagents or catalysts ... fluorobenzene, ...
The Balz–Schiemann reaction (also called the Schiemann reaction) is a chemical reaction in which a primary aromatic amine is transformed to an aryl fluoride via a diazonium tetrafluoroborate intermediate. [1] [2] [3] This reaction is a traditional route to fluorobenzene and some related derivatives, [4] including 4-fluorobenzoic acid. [5]
4-Fluorobromobenzene is synthesized via bromination of fluorobenzene in the presence of a Lewis acid catalyst such as iron(III) bromide or aluminium tribromide. [2]4-Bromofluorobenzene is regarded by the Toxic Substances Control Act as a high production volume chemical, that is, a chemical that 1 million pounds (about 500 tonnes) per year is either produced in or imported to the United States.
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 ...
Because inductive effects depends strongly on proximity, the meta and ortho positions of fluorobenzene are considerably less reactive than benzene. Thus, electrophilic aromatic substitution on fluorobenzene is strongly para selective. This -I and +M effect is true for all halides - there is some electron withdrawing and donating character of each.
The diazo group (N 2) can be replaced by many other groups, usually anions, giving a variety of substituted phenyl derivatives: . C 6 H 5 N 2 + + Nu − → C 6 H 5 Nu + N 2. These transformations are associated with many named reactions including the Schiemann reaction, Sandmeyer reaction, and Gomberg-Bachmann reaction.
Instead it is prepared by the reaction of alkali fluorides with halogenated benzene: [5] C 6 Cl 6 + 6 KF → C 6 F 6 + 6 KCl. Antimony fluoride instead adds to the ring, breaking aromaticity. [6]: 861 In principle, various halofluoromethanes pyrolyze to hexafluorobenzene, but commercialization was still in the initial stages in 2000. [7]: 21 ...