Fluorination of fluoro-cyclobutene with high-valency metal fluoride

Fluorinations of 1,4,4-trifluorocyclobutene and 3,3,4,4-tetrafluorocyclobutene using high-valency metal fluorides such as CoF3, MnF3, AgF2, CeF4 and KCoF4, and elemental fluorine were examined. In these reactions with CoF3 and MnF3, vic-difluorination proceeded mainly. While, 1,4,4-trifluorocyclobutene yielded 3,3,4,4-tetrafluorocyclobutene, and 3,3,4,4-tetrafluorocyclobutene yielded 1,3,3,4,4-pentafluorocyclobutene mainly in the case of AgF2. The further fluorinated products were increased under severer conditions. Also, the plausible reaction mechanism was suggested.

In the fluorinations of 1,4,4-trifluorocyclobutene and 3,3,4,4-tetrafluorocyclobutene with CoF3 and MnF3, vic-difluorination proceeded mainly. In contrast, the reactions using AgF2 proceeded in the different manner, and the unexpected cyclobutenes were formed mainly. Figure optionsDownload as PowerPoint slide