N. P. Bizier, J. P. Vernamonti, J. L. Katz
SHORT COMMUNICATION
7
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Experimental Section
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2
2
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[
4]arenes 3 and Diazadioxa[1
sphere, an air-dried flask was charged with aminophenol 2 or 4
0.245 mmol, 1 equiv.) and 1,5-difluoro-2,4-dinitrobenze (50.0 mg,
.245 mmol, 1 equiv.). DMSO (1.0 mL) was added, followed by
4
]cyclophanes 5: Under ambient atmo-
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(
0
CsF (369 mg, 2.45 mmol, 10 equiv.). The reaction mixture was
heated to 80 °C under a positive pressure of argon and stirred for
18 h. After cooling to room temperature, the product was precipi-
tated by the addition of water (10 mL) and 1 m HCl (1 mL). Un-
purified 3 or 5 was isolated by vacuum filtration, washed with water
(10 mL), and dried in vacuo. Macrocycle 3 or 5 was then dissolved
1
353.
in 7 mL of CH Cl , and stirred vigorously for 30 min. The solution
2
2
[
5] Synthesis of azacalixarenes by S Ar: a) Q.-Q. Wang, D.-X.
N
consisting of dissolved product was filtered, and the filtrate sub-
jected to flash column chromatography.
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Supporting Information (see footnote on the first page of this arti-
cle): Compound characterization for 3a–f and 5a–d, X-ray crystal-
lographic experimental data for 3a and 5b, and H NMR spectra
1
from mechanistic investigations.
Acknowledgments
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This work is supported by the National Science Foundation (CHE-
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0640729), the Petroleum Research Fund (45440-B1), and Colby
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may undergo conformational enantiomerization at ambient
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mational rigidification of the macrocycles, and resolution of
enantiomers will be addressed in a future manuscript.
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2306
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