Interaction of keramidonines with thiophenols

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

“…More recently, ceramidonines (e.g., 127.11 and 127.13 ) were obtained by direct benzyne cycloadditions to 1-aminoanthraquinone 127.9 . The requisite benzyne intermediates were generated from o -(trimethylsilyl)­phenyl triflate 127.10 by Rogness and Larock and from 5-arylthianthrenium perchlorates (e.g., 127.12 ) by Kim et al The reactivity of ceramidonines in electrophilic and nucleophilic substitutions was investigated, with a range of reagents being explored, such as amines, − active methylene compounds, arylsulfinic acids, alkoxides, potassium cyanide, and thiophenols . Functionalized ceramidonines containing s -triazine and sulfonamide groups were developed for use in dyeing.…”

“…The requisite benzyne intermediates were generated from o-(trimethylsilyl)phenyl triflate 127.10 by Rogness and Larock 696 and from 5-arylthianthrenium perchlorates (e.g., 127.12) by Kim et al 697 The reactivity of ceramidonines in electrophilic 698 and nucleophilic 699 substitutions was investigated, with a range of reagents being explored, such as amines, 700−710 active methylene compounds, 711 arylsulfinic acids, 712 alkoxides, 713 potassium cyanide, 714 and thiophenols. 715 Functionalized ceramidonines containing striazine 716 and sulfonamide 717 groups were developed for use in dyeing. Ceramidine derivatives of the general structure 146.14 were obtained by Wittig olefination of ceramidonine 127.11 by Lee et al 693 Sokolyuk and Pisulina reported a reversible photoarylotropic rearrangement of the ceramidonine derivative 127.7, in which the phenyl group could be induced to migrate between two adjacent oxygen atoms by alternating irradiation with UV and visible light.…”