Gas Liquid Chromatography-Mass Spectrometry of Paraquat and Diquat Reduction Products. A Reductive Cleavage of Paraquat and Diquat by NaBH_4 in the Presence of a Transition Metal Salt (Ni^<+2>)

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When herbicide preparations paraquat(I) and diquat(II), based on N-alkylbipyridylium derivatives, were analyzed by gas liquid chromatography (GLC) with sodium borohydride (NaBH_4)-nickel(II) chloride (NiCl_2) reduction, the chromatograms showed minor side peaks from slight amounts of by-products appearing in front of the main peaks, arising from the respective perhydrogenated products of I or II.Reductive cleavage of a C-N bond within each pyridine ring of I or II was suggested in view of the production of trifluoroacetic acid derivatives prepared from these by-products.The by-products, whose structures were elucidated by GLC-mass spectrometry, were consequently presumed to be p-(N-methylaminopent-3'-yl)-N-methylpiperidine, arising from I, or 1 butyl-2-aza-perhydroquinolizine, arising from II.Correlation was also observed between the amounts of NaBH_4 and NiCl_2 and the production of by-products; the less NaBH_4 and the more NiCl_2 in a given volume of water, the greater the increase in side reaction products.The side peaks could not be observed on the gas-chromatogram when perhydrogenated products prepared separately from I and II were treated by NaBH_4-NiCl_2 reduction. The side peaks could be observed, however, when incomplete reduction products with one or two double bonds, obtained by reduction of I and II by NaBH_4 alone, were reduced by NaBH_4-NiCl_2 reduction. It could therefore be presumed that this reductive cleavage at a C-N bond occurred, the intermediate state being the complex between nickel and incomplete reduction products with one or two remaining double bonds in the pyridine ring.
公益社団法人日本薬学会の論文
1991-04-25

Gas Liquid Chromatography-Mass Spectrometry of Paraquat and Diquat Reduction Products. A Reductive Cleavage of Paraquat and Diquat by NaBH_4 in the Presence of a Transition Metal Salt (Ni^<+2>)

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