Imine-Based Catechols and <i>o</i>-Benzoquinones: Synthesis, Structure, and Features of Redox Behavior
Tatyana V. Astaf'eva, Maxim V. Arsenyev, Roman V. Rumyantcev, Georgy K. Fukin, V.K. Cherkasov, Andrey I. Poddel’sky
Abstract
-benzoquinones react with water or methanol to yield products of water or methanol addition. A prototropic tautomerism is characteristic of catecholaldimines: a quinomethide form is observed in the case of aliphatic amine derivatives, while aryl-substituted catecholaldimines can exist both in the catechol and quinomethide forms in the crystalline state. The formation of dimeric structures motifs is observed in crystals. The electrochemical oxidation of imino-based catechols proceeds via two one-electron processes; the second wave is quasi-reversible, which is unusual for catechols.
Topics & Concepts
ChemistryCatecholQuinoneTautomerImineSteric effectsRedoxMethanolElectrochemistryAmine gas treatingMedicinal chemistryYield (engineering)ArylSemiquinonePhotochemistryOrganic chemistryStereochemistryCatalysisMaterials scienceMetallurgyElectrodePhysical chemistryAlkylPorphyrin and Phthalocyanine ChemistryAxial and Atropisomeric Chirality SynthesisBioactive Compounds and Antitumor Agents