Fluorination with Xenon Difluoride. 23. Fluorination of Ortho Substituted Aromatic Molecules

Article abstract of DOI:10.1246/bcsj.54.279

The fluorination of 9,10-dihydroxyanthracene and triptycene with xenon difluoride in the presence of hydrogen fluoride occured at α and β position with β attack predominating over α attack, while the reaction with acenaphthalene resulted in the formation of 2- and 4-fluorosubstituted products, regioselectivity being very little affected by the nature of the catalyst: hydrogen fluoride, boron trifluoride and pentafluorothiophenol.The fluorination of 1,2,3,4-tetrahydro-1,4-methanonaphthalene resulted in the formation of 6-fluoro-1,2,3,4-tetra-hydro-1,4-methanonaphthalene, 6,7-difluoro-1,2,3,4-tetrahydro-1,4-methanonaphthalene and rearranged product 1-(2,2-difluoroethyl)indan.