Interaction of perfluorobenzocycloalkenes with tetrafluoroethylene in the presence of SbF5

Formation and skeletal transformations of perfluoroindan-1-one and perfluoroindan-1,3-dione in the reaction of perfluoroindan with SiO2/SbF5

“…The formation of indanone 2 and diketone 3 can be rationalized by a mechanism involving the interaction of the perfluoroindan-1-yl cation initially generated [11] and perfluoroindan-3-one-1-yl cation with SiO 2 according to the Scheme 2.…”

Transformation of perfluorinated benzocycloalkenes and alkylbenzenes to their carbonyl derivatives under the action of CF3COOH/SbF5

“…Reaction of indan 3 with 2,2,3,3-tetrafluoropropan-1-ol in an SbF 5 medium at 20-50 8C forms a solution of a salt of 1-(2,2,3,3-tetrafluoropropoxy)-perfluoroindan-1-yl cation (5). Hydrolysis of the latter gives indanon 1.…”

“…For this purpose we have studied reactions of indan 3 with 2,2,3,3-tetrafluoropropanol, acetic and trifluoroacetic acids in the presence of SbF 5 . This work also describes reactions of ethylindan 4 and other aromatic fluorocarbons with CF 3 COOH/SbF 5 .…”

Expansion of the pentafluorobenzene ring of perfluoro-1,2-diethyl-1-phenylbenzocyclobutene under the action of SbF5

“…Previously, we have found and investigated the skeletal transformations of perfluoro-benzocycloalkenes (benzocyclobutene, indan and tetralin) and their perfluoroalkyl and perfluoroaryl derivatives in the reactions with antimony pentafluoride [1][2][3][4][5][6][7][8][9]. In these reactions perfluoroalkylbenzocyclobutenes undergo expansion of the four-membered ring to a five-membered ring; alternatively, the alicyclic ring cleavage of benzocyclobutenes leads to polyfluorostyrenes, which subsequently undergo cyclization into polyfluoroindans or fluorination [1,4,5].…”

“…In these reactions perfluoroalkylbenzocyclobutenes undergo expansion of the four-membered ring to a five-membered ring; alternatively, the alicyclic ring cleavage of benzocyclobutenes leads to polyfluorostyrenes, which subsequently undergo cyclization into polyfluoroindans or fluorination [1,4,5]. In perfluoro-1-(2-or 4-ethylphenyl)benzocyclobutenes under the action of SbF 5 both alicyclic and aromatic fragments of the substrate are involved in the reaction to give polyfluorinated fluorene or anthracene derivatives.…”