Synthesis, Molecular and Crystal Structures of Polyfluoroaryl-Substituted Aminodiaza- and Aminotriazadamantanes

Abstract

4-((5,7-Dimethyl-1,3-diazaadamantan-6-yl)amino)-2,3,5,6-tetrafluorobenzonitrile, 5,7-dimethyl-N-(2,3,5,6-tetrafluoro-4-nitrophenyl)-1,3-diazaadamantane-6-amine, 4-((1,3,5-triaza-adamantan-7-yl)amino)-2,3,5,6-tetrafluorobenzonitrile, and N-(2,3,5,6-tetrafluoro-4-nitrophenyl)-1,3,5-triaza-adamantane-7-amine are prepared by the interaction of 5,7-dimethyl-1,3-diazaadamantane-6-amine or 1,3,5-triazaadamantane-7-amine with the corresponding polyfluorinated aromatic compound (perfluorobenzonitrile or perfluoronitrobenzene). All the compounds are structurally characterized by NMR and IR spectroscopy, high-resolution mass spectrometry, and XRD. The structures of triazaadamantane derivatives, in contrast to substituted diazaadamantanes, contain multiple short F⋯F contacts.