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

TETRAHEDRON

卷:73

Article

Oliveira, Paulo F. M.^1,2  Haruta, Naoki³  Chamayou, Alain¹  Guidetti, Brigitte²  Baltas, Michel²  Tanaka, Kazuyoshi³  Sato, Tohru^3,4  Baron, Michel¹ 

[1] Univ Toulouse, CNRS, UMR 5302, Ctr RAPSODEE, Campus Jarlard, F-81013 Albi, France

[2] Univ Toulouse, Lab SPCMIB, CNRS, UMR 5068,UPS, 118 Route Narbonne, F-31062 Toulouse, France

[3] Kyoto Univ, Grad Sch Engn, Dept Mol Engn, Nishikyo Ku, Kyoto 6158510, Japan

[4] Kyoto Univ, Unit Elements Strategy, Initiat Catalysts & Batteries, Nishikyo Ku, Kyoto 6158510, Japan

关键词: Mechanochemistry;    Ball milling;    Reaction intermediates;    Reaction mechanism;    Diazines;   

DOI  :  10.1016/j.tet.2017.03.014

来源: Elsevier

【 摘 要 】

Compared mechanosynthesis of two condensed 1,4-diazines were investigated in ball milling conditions from o-phenylenediamine. C-13 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. (C) 2017 Elsevier Ltd. All rights reserved.

【 授权许可】

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