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  • Küçük Resim
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    ?,??-Diamino-p-quinodimethanes with three stable oxidation states
    (American Chemical Society, 2020) Mahata, Alok; Chandra, Shubhadeep; Maiti, Avijit; Rao, D. Krishna; Yıldız, Cem Burak; Sarkar, Biprajit; Jana, Anukul
    Herein, we report the rational design, synthesis, and characterization of ?,??-diamino-substituted-p-quinodimethanes, which are a group of partially substituted p-quinodimethanes. These exhibit two reversible one-electron redox steps and electrochromism in the ultraviolet, visible, and near-infrared regions. We were able to isolate the crystalline compounds of all three oxidation states: neutral, radical cation, and dication. The obtained results not only create the bridge between p-quinodimethane and ?,?,??,??-tetrasubstituted-p-quinodimethane, but also demonstrate the straightforward modular approach for the synthesis of ?-conjugated open-shell compounds.
  • Küçük Resim
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    Realizing 1,1-Dehydration of secondary alcohols to carbenes: pyrrolidin-2-ols as a source of cyclic (Alkyl)(Amino)carbenes
    (Wiley-VCH Verlag, 2022) Daş, Ayan; Elvers, Benedict J.; Nayak, Mithilesh Kumar; Chrysochos, Nicolas; Anga, Srinivas; Kumar, Amar; Rao, D. Krishna; Narayanan, Tharangattu N.; Schulzke, Carola; Yıldız, Cem Burak; Jana, Anukul
    Herein we report secondary pyrrolidin-2-ols as a source of cyclic (alkyl)(amino)carbenes (CAAC) for the synthesis of CAAC-Cu-I-complexes and cyclic thiones when reacted with Cu-I-salts and elemental sulfur, respectively, under reductive elimination of water from the carbon(IV)-center. This result demonstrates a convenient and facile access to CAAC-based Cu-I-salts, which are well known catalysts for different organic transformations. It further establishes secondary alcohols to be a viable source of carbenes-realizing after 185 years Dumas' dream who tried to prepare the parent carbene (CH2) by 1,1-dehydration of methanol. Addressed is also the reactivity of water towards CAACs, which proceeds through an oxidative addition of the O-H bond to the carbon(II)-center. This emphasizes the ability of carbon-compounds to mimic the reactivity of transition-metal complexes: reversible oxidative addition and reductive elimination of the O-H bond to/from the C(II)/C(IV)-centre.