The reaction of perfluoro-2,5-diazahexane 2,5-dioxyl with aromatic compounds and perfluoroiodoalkanes

Article abstract of DOI:10.1016/0022-1139(93)02911-W

Treatment of perfluoro-2,5-diazahexane 2,5-dioxyl (1) with the fluoroarenes C6F5X (X = F or Br at c. 20 deg C; X = CF3 at 50 deg C) and pentafluoropyridine (50 deg C) gives 2:1 copolymers in high yield, but pentachloropyridine is unreactive at 50 deg C.Copolymers are also formed between 1 and the arenes C6F5I, C6F5H and C6H6 which did not analyse correctly for 2:1 copolymers; in the latter case, hydrogen abstraction is taking place as shown by the presence of N-OH and C=O groups in the polymer.Hexafluorobenzene is not incorporated in the polymer formed by treatment of 1 with a mixture of vinylidene fluoride and hexafluorobenzene.Photochemical reaction of trifluoroiodomethane with 1 affords the bishydroxylamine CF3ON(CF3)CF2CF2N(CF3)OCF3 in quantitative yield, while the di-iodides I(CF2)nI (n = 2 and 4) give copolymers of 1 and the units (CF2)n (n = 2 and 4), which contain (CF2)nI end-groups.