Comprehensive experimental investigation of mechanically induced 1, 4-diazines synthesis in solid state. Issue 16 (20th April 2017)

• Record Type: Journal Article
• Authors: Oliveira, Paulo F.M.; Haruta, Naoki; Chamayou, Alain; Guidetti, Brigitte; Baltas, Michel; Tanaka, Kazuyoshi; Sato, Tohru; Baron, Michel
• Is Part Of: Tetrahedron. Volume 73:Issue 16(2017)
• Page Start: 2305
• Page End: 2310
• Publication Date: 2017-04-20
• Subjects: Mechanochemistry -- Ball milling -- Reaction intermediates -- Reaction mechanism -- Diazines; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.03.014
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Compared mechanosynthesis of two condensed 1, 4-diazines were investigated in ball milling conditions from o-phenylenediamine. 13 C 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. Graphical abstract: