Fluorination Reactions with HF/THF Medium Solvolysis of N-Tosyl-O-Phenylhydroxylamine
Solvolysis of N-tosyl-O-phenylhydroxylamine in HF/THF leads to regiospecific formation of p-fluorophenol via umpolung strategy which induces nucleophilic aromatic fluorine/hydrogen substitution.
Dolbier, William R.,Celewicz, Lech,Ohnishi, Keiichi
p. 4929 - 4930
(2007/10/02)
Acid-Catalyzed Solvolysis of N-Sulfonyl- and N-Acyl-O-arylhydroxylamines. Phenoxenium Ions
The acid-catalyzed reaction of N-acyl- and N-sulfonyl-O-arylhydroxylamines with benzene proceeded quite smoothly to give 2- and 4-hydroxybiphenyls.The results of product analysis, the orientation of the reaction, and the effects of substituents on the nitrogen atom and on the phenyl ring suggested a mechanism that involves a phenoxenium ion.The phenoxenium ion was trapped by benzene and other various nucleophiles.
Endo, Yasuyuki,Shudo, Koichi,Okamoto, Toshihiko
p. 6393 - 6397
(2007/10/02)
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