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

作者：Pittelkow Michael^*; Nielsen Christian B; Brock Nannestad Theis; Schau Magnussen Magnus; Christensen Jorn B

来源：European Journal of Organic Chemistry, 2012, (26): 4931-4936.

DOI：10.1002/ejoc.201200512

• Naphthalenes
• Density functional calculations
• peri-Effect
• Dimerization
• Arenes
• Radical ions

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.

• 出版日期2012-9