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Comprehensive experimental investigation of mechanically induced 1,4-diazines synthesis in solid state

Author:
Oliveira, Paulo F.M., Haruta, Naoki, Chamayou, Alain, Guidetti, Brigitte, Baltas, Michel, Tanaka, Kazuyoshi, Sato, Tohru, Baron, Michel
Source:
Tetrahedron 2017
ISSN:
0040-4020
Subject:
calorimetry, chemical reactions, chemical structure, milling, nuclear magnetic resonance spectroscopy, organic compounds
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.
Agid:
5643996