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1,4-Dicyanonaphthalene was obtained by heating a 1:4 mixture of 1,4-naphthalenedicarboxylic acid and urea to 215°C for 3 h; the residue was decolorized with a small amount of charcoal, and the product was recrystallized twice from EtOH (53%). This procedure was based on a nitrile synthesis found in Biggs, B. S.; Bishop, W. S. Organic Syntheses; Wiley: New York, 1955; Collect. Vol. III, pp 768-770.
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37049078385
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19
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14444272139
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note
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- deuterons over a period of weeks; the δ 1.85 proton exchanging faster than that at δ 2.10. This process presumably results from reversible opening of the oxazolidine ring to give the N-hydroxyethyliminium ion, followed by loss of either C-7 proton to give the corresponding enamine. We observed the base peak m/z 112 to decrease gradually and the peaks at m/z 113 and 114 to increase gradually as deuterium exchange took place.
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