Abstract

AbstractAn unusual peri‐dimerised product was obtained when subjecting 1,3,6,8‐tetramethoxynaphthalene to Vilsmeier–Haack reaction conditions (POCl3/DMF). The formation of this peri‐dimerised naphthalene product suggests that 1,3,6,8‐tetramethoxynaphthalene has comparable reactivity to that of Proton Sponge [1,8‐bis(dimethylamino)naphthalene]. The octamethoxy peri‐dimer was characterised using NMR spectroscopy, mass spectrometry, UV/Vis spectroscopy, Raman spectroscopy, electrochemistry, X‐ray crystallography and DFT calculations. The one‐electron oxidation of the peri‐dimerised naphthalene compound yielded a radical cation that was studied by EPR spectroscopy and UV/Vis spectroscopy at low temperatures. The experimental observations were confirmed by DFT calculations.

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