Detection of Explosive Nitroaromatics
FULL PAPER
Synthesis of 7,10-bis(4-bromophenyl)-8,9-bis[4-
thene (S3): A 15 mL pressure glass tube was charged with 7,10-bis(4-bro-
mophenyl)-8H-cyclopenta[a]acenaphthylen-8-one (0.102 g, 0.2 mmol) and
N
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1,2-bis[4-ACHTUNGTRENNUNG(hexyloxy)phenyl]ethyne (0.075 g, 0.28 mmol), to which a mini-
mal amount (approximately 1.5 mL) of 1,2,4-trichlorobenzene was added.
It was degassed by bubbling argon and sealed. The heterogeneous
purple-black solution was heated to 2208C with vigorous stirring until it
became homogeneous and took on a transparent greenish-yellow color
after 24 h. The reaction mixture was cooled in an ice bath and diluted
with hexane to precipitate the crude product, which was collected by fil-
tration and washed with copious amounts of ethanol. The resulting pale
yellow solid was then purified by passing it through a silica gel column
with 5% ethyl acetate/hexane mixture as eluent to yield pure S3 (92 mg,
52% yield). 1H NMR (400 MHz, CDCl3, 258C, TMS): d=7.73 (d, 3J-
´
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A
E
7.6 Hz, 2H), 7.17 (d, 3J
4H), 6.65 (d, 3J
(t, J
G
1.44–1.36 (m, 4H), 1.31 (s, 8H), 0.89 ppm (t, 3J
13C NMR (100 MHz, CDCl3, 258C, TMS): d=156.76, 140.69, 138.98,
136.38, 136.24, 136.12, 133.12, 132.06, 131.81, 131.66, 131.41, 129.66,
127.66, 126.69, 123.03, 120.96, 113.04, 67.70, 31.59, 29.18, 25.64, 22.53,
13.98 ppm; elemental analysis calcd (%) for C52H48Br2O2: C 72.22, H
5.59; found: C 72.14, H 5.74.
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Acknowledgements
The authors would like to acknowledge the NMR Research Centre, IISc
for NMR spectra. We would also like to thank Mr. K. Durga Prasad and
Prof. T. N. Guru Row for single-crystal XRD analysis. A financial grant
from DST and DIT is gratefully acknowledged.
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Received: May 18, 2012
Published online: && &&, 0000
Chem. Eur. J. 2012, 00, 0 – 0
ꢀ 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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