UNSATURATED NITROGEN COMPOUNDS CONTAINING FLUORINE. PART 8. THE REACTION OF 2,5-DICHLORO-1,1,1,6,6,6-HEXAFLUORO-3,4-DIAZAHEXA-2,4-DIENE WITH TRIETHYLAMINE AND RELATED REACTIONS

Article abstract of DOI:10.1016/S0022-1139(00)80291-2

Exposure of a mixture of the title azine (1) and triethylamine (1:2 molar ratio) to daylight gives as major products, triethylamine hydrochloride and the Δ²-azetine (3), together with trifluoroacetonitrile and tar; a single electron transfer (SET) mechanism is proposed involving the intermediacy of the enamine Et2NCH=CH2.In contrast the reaction of azine (1) with tri-n-propylamine in light affords the amine hydrochloride, the substituted azine CF3CCl=N-N=C(NPrⁿ2)CF3 (14) and tar.Treatment of the heterocycle (3) with diethylamine results in replacement of Cl by NEt2 to give the azetine (6) which is also formed when the azine CF3CCl=N-N=C(NEt2)CF3 (7) is heated with triethylamine.