Diels–Alder reactions of polyfluorocyclohexa-1,3-dienes. Part V. Addition of cycloalkenes to octafluorocyclohexa-1,3-diene and dehydrofluorination of some of the adducts

Abstract

perfluorocyclohexa-1,3-diene (6) gives the expected Diels–Alder adducts with cyclohexene, cyclopentene, 1H,2H-octafluorocyclohexene, 1H,2H-hexafluorocyclopentene, and 1H,2H-tetrafluorocyclobutene; in the case of 1H,2H-tetrafluorocyclobutene two 2,2-difluorovinyldecafluorobicyclo[2,2,2]oct-2-enes and the dimer, 3,3,4,4,7,7,8,8-octafluorotricyclo[3,3,0,0^2,6]octane (4), were also isolated. Dehydrofluorination of the adducts formed from 1H,2H-octafluorocyclohexene and 1H,2H-hexafluorocyclopentene gave perfluorotricyclo[6,2,2,0^2,7]-dodeca-2,6,9-triene (10) and perfluorotricyclo[5,2,2,0^2,6]undeca-2,5,8-triene (8), respectively.