ChemInform Abstract: FLUORINATION WITH XENON DIFLUORIDE. 23. FLUORINATION OF ORTHO SUBSTITUTED AROMATIC MOLECULES

The fluorination of 9,10-dihydroanthracene and triptycene with xenon difluoride in the presence of hydrogen fluoride occurred at α and β position with β attack predominating over α attack, while the reaction with acenaphthene 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-tetrahydro-1,4-methanonaphthalene, 6,7-difluoro-1,2,3,4-tetrahydro-1,4-methanonaphthalene and rearranged product 1-(2,2-difluoroethyl) indan.