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A peri ‐Cyclised Naphthalene Dimer: Synthesis and Properties of an Unusual Vilsmeier–Haack Product of 1,3,6,8‐Tetramethoxynaphthalene
Author(s) -
Pittelkow Michael,
Nielsen Christian B.,
BrockNannestad Theis,
SchauMagnussen Magnus,
Christensen Jørn B.
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200512
Subject(s) - chemistry , naphthalene , dimer , raman spectroscopy , spectroscopy , ultraviolet visible spectroscopy , reactivity (psychology) , electron paramagnetic resonance , nuclear magnetic resonance spectroscopy , mass spectrometry , photochemistry , medicinal chemistry , crystallography , organic chemistry , nuclear magnetic resonance , medicine , physics , alternative medicine , pathology , quantum mechanics , chromatography , optics
An unusual peri ‐dimerised product was obtained when subjecting 1,3,6,8‐tetramethoxynaphthalene to Vilsmeier–Haack reaction conditions (POCl 3 /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.