422-98-0Relevant articles and documents
Conversion of Fluorocarbon Olefins into Perfluoro-ketoximes
Banks, Ronald E.,Dickinson, Neil
, p. 97 - 100 (1982)
Treatment of perfluoro-2-nitrosopropane and perfluoronitrosocyclobutane with aqueous potassium bisulphite yields the oximes of perfluoroacetone and perfluorocyclobutanone, respectively; the nitroso-compounds are easily prepared via indirect addition of nitrosyl fluoride across the double bonds in perfluoropropene and perfluorocyclobutene.
Fluorocarbon Derivatives of Nitrogen. Part 6. Reactions of Some Perfluorinated Nitroso-compounds with Hydrogen Sulphite Ion: Conversion of Fluorocarbon Olefins into Perfluoro-ketone Oximes
Banks, Ronald E.,Dickinson, Neil
, p. 685 - 688 (2007/10/02)
The sequence of events R1FR2FCFNO + HSO3-aq. -> R1FR2FCFN(OH)SO3- -> R1FR2FCFNHOH -> R1FR2FC=NOH is proposed to account for the production of N-trifluoromethylhydroxylamine, perfluoropropanohydroximoyl fluoride, perfluoroacetone oxime, and perfluorocyclobutanone oxime when the nitroso-compounds CF3NO, n-C3F7NO, (CF3)2CFNO, and (*)CF2CF2CF2C(*)FNO, respectively, are treated with aqueous potassium hydrogen sulphite; understandably, perfluoro-1-nitrosopropane reacts with the same reagent in the presence of lead(IV) oxide to give the purple water-soluble oxyl n-C3F7N(O.)SO3-K+.Since perfluoro-2-nitrosopropane and perfluoronitrosocyclobutane are easily obtained via the route R1FCF=CFRF -> (with KF-CF3CO2Ag)R1FCFAgCF2RF -> (with NOCl) R1FCF(NO)CF2RF (R1F = CF3, RF = F; R1FRF = CF2CF2)(RFCF2 = R2F), the reductive defluorination with aqueous hydrogen sulphite anion completes a fluorocarbon olefin -> fluorocarbon ketone oxime conversion.