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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 31, Number 4
BKCSDE 31(4)
April 20, 2010 

Synthesis and Structure of Benzotriazolyl Fluorenes
Kwanghee Koh Park*, Hyemi Jung, Taewoo Lee, Sung Kwon Kang
2-Aminofluorenes, 2-(N-2,4-Dinitrophenyl)aminofluorenes, 2-(N-2,4-Diaminophenyl)aminofluorenes,
1-(Fluoren-2-yl)-benzo[d][1,2,3]triazoles, 7-Benzotriazol-1-yl-fluorene-2-sulfonic acids
1-(Fluoren-2-yl)-benzo[d][1,2,3]triazoles 5a-b were synthesized starting from 2-nitrofluorene. 2-Nitrofluorenes 1a-b were reduced by catalytic hydrogenation, reacted with 2,4-dinitrofluorobenzene followed by catalytic hydrogenation to afford 2-(N-2,4-diaminophenyl)aminofluorenes 4a-b. Diazotization of 4a-b with NaNO2/H2SO4 followed by treatment with H3PO2 gave 5a-b. Sulfonation of 5a-b yielded 7-benzotriazol-1-yl-fluorene-2-sulfonic acids 6a-b. The structures of 5b and 6b were firmly identified by X-ray crystal analysis in addition to 1H NMR, 13C NMR, and elemental analysis.
984 - 988
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