- Conversion of Fluorocarbon Olefins into Perfluoro-ketoximes
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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.
- Banks, Ronald E.,Dickinson, Neil
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- FLUOROCARBON DERIVATIVES OF NITROGEN. PART 10. PREPARATION OF HEPTAFLUORO- AND 1-CHLOROHEXAFLUORO-2-NITROSOPROPANE, AND CONVERSION OF THE LATTER TO CHLOROPENTAFLUOROACETONE OXIME
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Details are given for the preparation of heptafluoro-2-nitrosopropane and 1-chlorohexafluoro-2-nitrosopropane via the routes CF3CF=CF2 ->FCO2Ag (RF = CF3, n-C3F7)> (CF3)2CFAg -> (with NOCl) (CF3)2CFNO and CF3CF=CF2 -> (with CsCl-NOCl) CF3(CF2Cl)CFNO, respectively, and for conversion of the latter nitroso-compound to chloropentafluoroacetone oxime via reduction with aqueous potassium hydrogen sulphite.
- Banks, Ronald E.,Dickinson, Neil,Morrissey, Alan P.,Richards, Adrian
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- Fluorocarbon Derivatives of Nitrogen. Part 6. Reactions of Some Perfluorinated Nitroso-compounds with Hydrogen Sulphite Ion: Conversion of Fluorocarbon Olefins into Perfluoro-ketone Oximes
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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.
- Banks, Ronald E.,Dickinson, Neil
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p. 685 - 688
(2007/10/02)
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