The synthesis of new functionalized 1,3,5-triazine-based stable bi- and trinitroxides of the 2,5-dihydroimidazole series

Abstract

New non-conjugated functionalized 2,5-dihydroimidazole-type bi-and trinitroxyl radicals are described. The synthesis of which was based on a nucleophilic substitution reaction between 2,4,6-trichloro-1,3,5-triazine or 2,4-dichloro-6-methoxy-1,3,5-triazine and spiro-fused 2,5-dihydroimidazole-type monoradicals bearing both a p-hydroxyaryl moiety at the C-4 atom of the heterocycle and a residue at the fourth position of the cyclohexane ring. The model tris-nitroxide with an unsubstituted cyclohexane unit was structurally characterized in the solid state.

Spirocyclic Nitroxides as Versatile Tools in Modern Natural Sciences: From Synthesis to Applications. Part I. Old and New Synthetic Approaches to Spirocyclic Nitroxyl Radicals

“…Symmetric triradicals 256a–c have been synthesized upon treatment of cyanuric chloride 255 with three equivalent of SNR 251 (X = H; O(C=O)Ar, p -C 6 H 4 -O(C=O)Ar) in an attempt to prepare liquid crystalline discotics based on s -triazine ( Scheme 44 ). The crystal structure of triradical 256a has been determined by the X-ray diffraction method [ 161 ].…”