460-49-1Relevant articles and documents
The reaction of perfluoro-2,5-diazahexane 2,5-dioxyl with aromatic compounds and perfluoroiodoalkanes
Green, Michael J.,Tipping, Anthony E.
, p. 237 - 242 (2007/10/02)
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.
Reactions of Perfluoronitroxides with Sulphur Dioxide
Arfaei, Ahmad,Smith, Sydney
, p. 1791 - 1794 (2007/10/02)
Perfluoro-2,5-diazahexane 2,5-dioxyl reacts with sulphur dioxide and with sulphur tetrafluoride to give the 1 : 1 cyclic adducts perfluoro(4,7-dimethyl-1,3-dioxa-2-thia-4,7-diazacycloheptane 2,2-dioxide) and perfluoro(4,7-dimethyl-1,3-dioxa-2-tetrafluorothia-4,7-diazacycloheptane), respectively.Perfluoro(4,7-dimethyl-1,3-dioxa-2-thia-4,7-diazacycloheptane 2,2-dioxide) which oxidises iodide ion to iodine at room temperature, is stable to hydrolysis by aqueous potassium hydroxide at 120 deg C.It is stable to u.v. irradiation, but flow pyrolysis at 350 deg C and ca. 1 mmHg pressure gives trifluoronitrosomethane, perfluoro(2-methyl-1,2-oxazetidine), carbonyl fluoride, perfluoro(N-methylenemethylamine), and sulphur dioxide.It reacts with triphenylphosphine to give perfluoro(3,6-dimethyl-1-oxa-2-thia-3,6-diazacyclohexane 2,2-dioxide), perfluoro(2,5-dimethyl-1-thia-2,5-diazacyclopentane 1,1-dioxide) and triphenylphosphine oxide.Bis(trifluoromethyl) nitroxide reacts with sulphur dioxide to give the 2 : 1 adduct perfluoro(2,6-dimethyl-3,5-dioxa-4-thia-2,6-diazaheptane 4,4-dioxide), flow pyrolysis of which at 350 deg C and ca. 1 mmHg gives only bis(trifluoromethyl) nitroxide and sulphur dioxide.Perfluoro(2,4-dimethyl-3-oxa-2,4-diazapentane) reacts with sulphur dioxide giving perfluoro(2,5-dimethyl-3-oxa-4-thia-2,5-diazahexane 4,4-dioxide).
Fluorocarbon Derivatives of Nitrogen. Part 5. Replacement of Imidoyl Halogen by the Bistrifluoromethylamino-oxy Group : Reactions of Perfluoro-2-azapropene and Related Compounds with Bis(bistrifluoromethylamino-oxy)mercury(II) or NN-Bistrifluoromethylhydroxylamine-Caesium Fluoride
Banks, Ronald E.,Choudhury, Dilip R.
, p. 1443 - 1447 (2007/10/02)
Treatment of perfluoro-2-azapropene with bis(bistrifluoromethylamino-oxy)mercury(II) yields the new mercurial (CF3)N>2Hg (11), chlorinolysis of which provides the N-chloroamine CF3NClCF2ON(CF3)2 (16); pyrolysis of the mercurial (11) gives a complex mixture containing the imine CF3N=CFON(CF3)2 (12) and material tentatively identified as >2O.The N-chloro-compound (16) reacts with hydrogen chloride and silver cyanide to provide the corresponding amine CF3NHCF2ON(CF3)2 and the related imine (12).The latter product, together with the di-substituted analogue (CF3)2NCF2N=CFON(CF3)2, can also be procured by treating perfluoro-2-azapropene with a caesium fluoride-NN-bistrifluoromethylhydroxylamine adduct.This reagent also attacks perfluoro-1-azacyclohexene to yield perfluoro- and perfluoro-, and similarly effects nucleophilic substitution in pentafluoropyridine to provide 4-(bistrifluoromethylamino-oxy)-2,3,5,6-tetrafluoropyridine.The mercurial 2Hg attacks the alkyliminocarbonyl chloride Me3CN=CCl2 to give the bistrifluoromethylamino-oxy-derivatives Me3CN=CCl and Me3CN=C2.
