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Abstract
Compared mechanosynthesis of two condensed 1,4-diazines were investigated in ball milling conditions from o-phenylenediamine. 13C CP-MAS NMR revealed a hemiaminal intermediate for dibenzo[a,c]phenazine synthesis accumulated under mechanical action, as confirmed by calorimetry. Such intermediate, which is not detected in the case of 2,3-diphenylquinoxaline synthesis, provides experimental evidence of a concerted reaction between highly reactive mechanically-excited diamine and 9,10-phenanthrenequinone.
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