POLYFLUOROCYCLOALKENES. PART XIX. SOME REACTIONS AND COMPOUNDS FROM 1,2-BIS(TRIFLUOROMETHYL)OCTAFLUOROCYCLOHEXENE

Article abstract of DOI:10.1016/S0022-1139(00)81941-7

The title compound (A) gave a dichloro-adduct (D), which with lithium aluminum hydride yielded a complex mixture, from which a trace of trans 1H,2H-1,2-bis(trifluoromethyl)octafluorocyclohexane (E) was isolated.Catalytic hydrogenation of olefin (A) afforded cis 1H,2H-1,2-bis(trifluoromethyl)octafluorocyclohexane (C), and a small amount of 6H-1,6-bis(trifluoromethyl)heptafluorocyclohexene (B).Dehydrofluorination of the cis dihydride (C) by aqueous potash gave olefin (B) and 2,3-bis(trifluoromethyl)hexafluorocyclohexa-1,3-diene (G): fluorination of (G) by cobalt(III) fluoride gave back (A).Fluorination of compounds (C) and (B) afforded cis and trans 1H-1,2-bis(trifluoromethyl)nonafluorocyclohexane (J and H respectively).Both (H) and (J) were dehydrofluorinated to give olefin (A) exclusively, i.e. fluorine was lost preferentially from the tertiary ->C-F group.Ammonia and (A) gave 1,3-diamino-2-cyano-3-trifluoromethylhexafluorocyclohexene (K).Some hydro-polyfluoro-cyclohexanes took up small proportions of deuterium during dehydrofluorinations in the presence of deuterium oxide,but no interconversions of pairs of stereoisomers were observed.