FLUOROINDENES. 13. TRANSFORMATIONS OF POLYFLUORINATED INDENES AND 1-ALKYLIDENEINDANS IN THE H2O2-HF-SbF5 SYSTEM

Article abstract of DOI:10.1007/BF00866597

The reaction of perfluorinated indene, 3-methylindene, and 1-methylene- and 1-ethylideneindans with hydrogen peroxide in the hydrogen fluoride-antimony pentafluoride medium takes place at the multilple bond of the substrate and leads to the oxo derivatives of indan.The process probably takes place through the electrophilic addition of HO⁺.The C=C bond in perfluoro-3-methylindenone is not affected.In this compound and also in perfluoro-2-indanone and perfluoro-1-methyl-2-indanone the carbonyl group is involved in reaction with hydrogen peroxide in the HF-SbF5 system, and six-membered oxygen-containing heterocyclic compounds are formed.Keywords: Polyfluorinated indenes, alkylindeneindans, electrophilic hydroxyfluorination, polyfluorinated ketones, Bayer-Villiger reaction.