Reactions of tetracyclic tetraaminophosphoranes with dichloroperfluoro cyclic and acyclic alkenes and halo compounds

Abstract

Cyclenphosphorane was reacted with 1,2-dichlorotetrafluorocyclobutene-1, 1,2-dichlorohexafluorocyclopentene-1, 1,2-dichlorooctafluorocyclohexene-1, iodopentafluorobenzene, 2-iodo-1,1,1-trifluoroethane, and 2,3-dichlorohexafluorobutene-2 in the presence of triethylamine at room temperature in tetrahydrofuran to form monochlorotetrafluorocyclobutenylcyclenphosphorane, monochlorohexafluorocyclopentenylcyclenphosphorane, monochlorooctafluorocyclohexenylcyclenphosphorane, pentafluorophenylcyclenphosphorane, 1,1,1-trifluoroethylcyclenphosphorane, and 2-chlorohexafluorobut-2-enylcyclenphosphorane in 70–80% yields, respectively. Cyclamphosphine oxide reacted with dichloroperfluorocyclic alkenes in the presence of triethylamine in chloroform to form N-(chlorotetrafluorocyclobutenyl)cyclamphosphine oxide, N-(chlorohexafluorocyclo-pentyl)cyclamphosphine oxide and N-(chlorooctafluorocyclohexenyl)-cyclamphosphine oxide in ∼50% yields, respectively. These moisture sensitive cyclamphosphine oxide derivatives are stable and are soluble in CHCl 3, CH 3CN and DMSO.