New highly fluorinated phenazine derivatives: Correlation between crystal structure and NMR spectroscopy

New highly fluorinated derivatives of phenazine which are difficult to obtain in other ways, namely 1,2,2,3,4-pentafluoro-10-(2,3,4,5,6-pentafluorophenyl)-2,10-dihydrophenazine (2) and its hydrolyzed product 1,3,4-trifluoro-10-(2,3,4,5,6-pentafluorophenyl)-2(10H)-phenazinone (3), were both synthesized and characterized by means of single-crystal X-ray analysis and 1H, 19F NMR spectroscopy. Correlation between the results of X-ray analysis and NMR spectroscopy is established. The formation mechanism of 2 involving oxidation of a cobalt complex bearing two noninnocent o-benzosemiquinonediiminato(1-) ligands is proposed.

Graphical abstractSynthesis of two new phenazine derivatives and their X-ray structures are reported. Figure optionsDownload full-size imageDownload as PowerPoint slide