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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 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]
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.
Difluorobenzenes can be prepared by the Balz-Schiemann reaction, which entails conversion of diazonium tetrafluoroborate salts to their fluorides. The synthesis of 1,2-difluorobenzene starts with 2-fluoroaniline: [3] C 6 H 4 F(NH 2) + HNO 2 + HBF 4 → [C 6 H 4 F(N 2)]BF 4 + 2 H 2 O [C 6 H 4 F(N 2)]BF 4 → C 6 H 4 F 2 + N 2 + BF 3
If the benzene ring contains other substituents, it belongs in Category:Fluorobenzene derivatives The main article for this category is Fluorobenzenes . Pages in category "Fluorobenzenes"
An individual reaction can be described as: R 3 C–H + HF → R 3 C–F + H 2. In the course of a typical synthesis, this reaction occurs once for each C–H bond in the precursor. The cell potential is maintained near 5–6 V. The anode is nickel-plated.
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