Abstract
Although the direct anodic fluorination of 3-phenyl-2H -1,4-benzoxazine was not very effective,
the fluorodesulfurization of 3-aryl-2-(phenylsulfanyl)-2H -1,4-benzoxazines using various anodically
generated halogen mediators in the presence of triethylamine
tris(hydrogen fluoride) by an ex-cell method efficiently and selectively
provided the corresponding monofluorinated products. In sharp contrast,
in-cell halogen mediators did not work well. Furthermore, the selective
fluorodesulfurization of pyrido[3,2-b ][1,4]oxazine
derivatives was also successfully carried out using the same ex-cell
method to provide the corresponding monofluorinated products in
moderate yields.
Key words
halogenation - fluorine - heterocycles - electron
transfer - oxidations
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