Fluorocarbon derivatives of nitrogen. Part 6. Reactions of some perfluorinated nitroso-compounds with hydrogen sulphite ion: conversion of fluorocarbon olefins into perfluoro-ketone oximes
- 1 January 1982
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 685-688
- https://doi.org/10.1039/p19820000685
Abstract
The sequence of events R1 FR2 FCFNO + HSO3 – aq. → R1 FR2 FCFN(OH)SO3 –→ R1 FR2 FCFNHOH → R1 FR2 FCNOH 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 [graphic omitted]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 R1 FCFCFRF→(with KF–CF3CO2Ag) R1 FCFAgCF2RF→(with NOCl) R1 FCF(NO)CF2RF(R1 F= CF3, RF= F; R1 FRF= CF2CF2)(RFCF2= R2 F), the reductive defluorination with aqueous hydrogen sulphite anion completes a fluorocarbon olefin → fluorocarbon ketone oxime conversion.Keywords
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