One-pot synthesis of perfluorinated benzenedithiols from perfluoroarenes and thioacetic acid

The direction of the reaction between substituted perfluorobenzenes and thioacetic acid depends on the location of the substituents in perfluoroaromatic ring. Hexafluorobenzene reacts at positions 1 and 4, perfluoro-m-xylene reacts at positions 4 and 6, while perfluoroindane reacts at positions 5 and 6 to give the corresponding dithiols with para-, meta- and ortho-location of the thiol groups, respectively. Domino-reaction of perfluoroindane-5-thiol and its acetyl thioester affords hexadecafluoro-2,12-dithia-pentacyclo[11.7.0.0^3,11.0^5,9.0^15,19]icosa-1(13),3,5(9),10,14,19-hexaene