Towards Norcorrin: Hydrogenation Chemistry and the Heterodimerization of Nickel(II) Norcorrole

5,14-Dimesitylnorcorrolatonickel(II) was hydrogenated under mild conditions (room temperature, 1atm H-2, THF solution, 5min.) in the presence of Raney nickel to yield nonaromatic derivatives that were isolated and characterized by NMR spectroscopy, UV/Vis spectrophotometry, HRMS, cyclic voltammetry, and X-ray diffraction analysis. The major hydrogenation product, 1,2,3,7,8,9-hexahydronorcorrolatonickel(II), underwent dimerization in the presence of p-chloranil to give a nonsymmetrically linked 2,3-bis(norcorrole) system that can adopt eight different oxidation states over a redox potential window of 3V and has a HOMO-LUMO gap of 0.92V.