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36549041093
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note
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Typical procedure: a mixture of 3,3,6,6-tetrachloro-2,2-dihydroxycyclohexanone 1 (3.8 mmol), the corresponding o-phenylenediamine 2 (3.8 mmol), triethylamine (14 mmol), and chloroform (50 mL) was stirred for 5 h at 45 °C. After evaporation to dryness under reduced pressure, water (150 mL) was added and the mixture was extracted with chloroform (3 × 60 mL). The combined extracts were washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure giving a solid residue that provided highly pure phenazines 3 by either direct crystallization in the appropriate solvent (3a,b) or by column chromatography (3c,d; silica gel/ethyl acetate-hexane, ratio 3:1).
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23
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36549052295
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note
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The procedure followed by us to prepare this compound is reported as Supplementary data.
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24
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36549066926
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note
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Tables of fractional atomic coordinates, thermal parameters, bond lengths and angles have been deposited at the Cambridge Crystallographic Center (CCDC 607589).
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32
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36549029393
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note
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The starting material 1 was recovered unaltered from experiments under the same preparative experimental conditions but in the absence of o-phenylenediamine.
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