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    Disclosing Cyclic(Alkyl)(Amino)Carbenes as a One-Electron Reductant: Synthesis of Acyclic(Amino)(Aryl)Carbene-Based Kekulé Diradicaloids
    (Wiley, 2023) Maiti, Avijit; Elver, Benedict J.; Bera, Sachinath; Lindl, Felix; I-Krummenacher, Ivo; Krummenacher, Ivo; Ghosh, Prasanta; Yıldız, Cem Burak; Braunschweig, Holger; Schulzke, Carola; Jana, Anukul
    Herein we disclose cyclic(alkyl)(amino)carbenes (CAACs) as a one-electron reductant under the formation of a transient radical cation as indicated by EPR spectroscopy. Subsequently, the disclosed CAAC reducing reactivity was utilized for the synthesis of acyclic(amino)(aryl)carbene-based Thiele and Chichibabin hydrocarbons, a new class of Kekulé diradicaloids. The results demonstrate the CAAC to be a potent organic reductant. Notably, the acyclic(amino)(aryl)carbene-based Chichibabin's hydrocarbon shows an appreciable population of the triplet state at room temperature, as evidenced by both variable temperature NMR and EPR spectroscopy.