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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 18, Number 6
BKCSDE 18(6)
June 20, 1997 

Cation Radicals with 2-Pyridylhydrazones in Nitrile Solvents s-Triazolo[4,3-α]pyridines by Thianthrene Cation Radical Perchlorate and 1-(2-Pyridyl)-1,2,4-Triazoles by Tris(2,4-Dibromophenyl)aminium Hexachloroantimonate
Koon Ha Park, Kun Jun, Seung Rim Shin, Sea Wha Oh
Reactions of arenealdehyde 2-pyridylhydrazones (1) with thianthrene cation radical (Th+·) and tris(2,4-dibromophenyl)aminium hexachloroantimonate (Ar3N+·SbCl6-) 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 Ar3N+·, respectively in nitrile solvents. The plausible mechanisms are proposed based on both the reduction potentials of Th+· and Ar3N+· and control experiments.
604 - 608
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