Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Cation Radicals with 2-Phridylhydrazones in Nitrile Solvents s-Triazolo[4,3-a]pyridines by Thianthrene Cation Radical Perchlorate and 1-(2-Pyridyl)-1,2,4-Triazoles by Tris(2,4-Dibromophenyl)-aminium Hexachloroantimonate

  • Published : 1997.06.20
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Abstract

Reactions of arenealdehyde 2-pyridylhydrazones (1) with thianthrene cation radical ($Th^{+·}$) and tris(2,4-dibromophenyl)aminium hexachloroantimonate ($Ar_3N^{+·}SbCl_6^-$) were investigated. The major product was switched depending on the cation radical being used. That is, s-triazolo[4,3-α]pyridines (2), an intramolecular cyclization product, and 1-(2-pyridyl)-1,2,4-triazoles (3), an intermolecular cycloaddition product, were obtained as a major product when reacted with $Th^{+·}$ and $Ar_3N^{+·}$, respectively in nitrile solvents. The plausible mechanisms are proposed based on both the reduction potentials of $Th^{+·}$ and $Ar_3N^{+·}$ and control experiments.

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References

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