A peri-Cyclised Naphthalene Dimer: Synthesis and Properties of an Unusual Vilsmeier-Haack Product of 1,3,6,8-Tetramethoxynaphthalene

[摘要]：An unusual peri-dimerised product was obtained when subjecting 1,3,6,8-tetramethoxynaphthalene to VilsmeierHaack 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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