POLYFLUOROCYCLOALKENES. PART XVIII. ARYL ADDUCTS OF DECAFLUOROCYCLOHEXENE

Article abstract of DOI:10.1016/S0022-1139(00)81135-5

Decafluorocyclohexene reacted slowly with aniline to give 1-phenylamino-3-phenyliminoheptafluorocyclohex-1-ene, which was hydrolysed by hydrochloric acid to 3-phenylaminoheptafluorocyclohex-2-enone.Decafluorocyclohexene reacted stepwise with phenyl lithium, giving 1-phenylnonafluorocyclohexene and thence 1,2-diphenyloctafluorocyclohexene: the former product was attacked slowly by pentafluorophenyl lithium at -40 deg C affording 1-pentafluorophenyl-1-phenyloctafluorocyclohexene.Phenyl lithium reacted sluggishly with bis(pentafluorophenyl)octafluorocyclohexene to give 1-pentafluorophenyl-2-(2',3',5',6'-tetrafluoro-1'-biphenylyl)octafluorocyclohexene and 1,2-bis(2',3',5',6'-tetrafluoro-1'-biphenyl)octafluorocyclohexene. 1,2-Diphenyloctafluorocyclohexene and 1,2-bis(pentafluorophenyl)octafluorocyclohexene were fluorinated by cobalt(III) fluoride to give the olefin, 1,2-bis(undecafluorocyclohexyl)octafluorocyclohexene.