The Preparation of p-Fluorophenols from p-Aminophenols: Diazotization and Fluorodiazoniation in Pyridine-HF.
A facile preparation of p-fluorophenols is described by the diazotization of p-aminophenols and fluorodediazoniation in situ using HF in a pyridine solution (pyridine-HF) under carefully controlled conditions.
Facile preparation of aromatic fluorides by deaminative fluorination of aminoarenes using hydrogen fluoride combined with bases
One-pot deaminative fluorination of aminoarenes including heteroaromatics, namely, diazotization of aminoarenes followed by in situ fluoro-dediazoniation of the corresponding diazonium ions, was successfully accomplished to produce fluoroarenes in high yields by using hydrogen fluoride combined with base solutions. The diazotization stage has been found to play the most important part in yielding fluoroarenes effectively. It was greatly influenced by the composition of the HF solution and enhanced by employing appropriate amounts of bases such as pyridine under carefully controlled conditions. The fluoro-dediazoniation stage was effectively accelerated photochemically to afford fluoroarenes having polar substituents such as hydroxyl, nitro and so on in high yields.
Yoneda,Fukuhara
p. 23 - 36
(2007/10/02)
Synthesis of Polynitrodiazophenols
The formation of diazophenols by nitration of suitably substituted anilines and rearrangement of the nitroaromatic nitramines so formed is presented.The scope of the reaction is discussed, and a mechanism for the nitramine/diazophenol rearrangement is proposed which is consistent with 15N-labeling experiments.
Atkins, Ronald L.,Wilson, William S.
p. 2572 - 2578
(2007/10/02)
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