A peri-cyclised naphthalene dimer: synthesis and properties of an unusual vilsmeier-haack product of 1,3,6,8-tetramethoxynaphthalene

Michael Pittelkow; Christian Benedikt Nielsen; Theis Brock-Nannestad; Magnus Schau-Magnussen; Jørn Bolstad Christensen

doi:10.1002/ejoc.201200512

A peri-cyclised naphthalene dimer: synthesis and properties of an unusual vilsmeier-haack product of 1,3,6,8-tetramethoxynaphthalene

Michael Pittelkow, Christian Benedikt Nielsen, Theis Brock-Nannestad, Magnus Schau-Magnussen, Jørn Bolstad Christensen

Department of Chemistry

2 Citations (Scopus)

Abstract

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. The Vilsmeier-Haack reaction (POCl ₃/DMF) of 1,3,6,8-tetramethoxynaphthalene gave an unusual peri-cyclised dimer as well as the 1-naphthaldehyde. The dimer is a potent donor molecule.

Original language	English
Journal	European Journal of Organic Chemistry
Volume	2012
Issue number	26
Pages (from-to)	4931-4936
Number of pages	6
ISSN	1434-193X
DOIs	https://doi.org/10.1002/ejoc.201200512
Publication status	Published - Sept 2012

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A peri-cyclised naphthalene dimer: synthesis and properties of an unusual vilsmeier-haack product of 1,3,6,8-tetramethoxynaphthalene. / Pittelkow, Michael; Nielsen, Christian Benedikt; Brock-Nannestad, Theis et al.
In: European Journal of Organic Chemistry, Vol. 2012, No. 26, 09.2012, p. 4931-4936.

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title = "A peri-cyclised naphthalene dimer: synthesis and properties of an unusual vilsmeier-haack product of 1,3,6,8-tetramethoxynaphthalene",

abstract = "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. The Vilsmeier-Haack reaction (POCl 3/DMF) of 1,3,6,8-tetramethoxynaphthalene gave an unusual peri-cyclised dimer as well as the 1-naphthaldehyde. The dimer is a potent donor molecule.",

author = "Michael Pittelkow and Nielsen, {Christian Benedikt} and Theis Brock-Nannestad and Magnus Schau-Magnussen and Christensen, {J{\o}rn Bolstad}",

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T2 - synthesis and properties of an unusual vilsmeier-haack product of 1,3,6,8-tetramethoxynaphthalene

AU - Pittelkow, Michael

AU - Nielsen, Christian Benedikt

AU - Brock-Nannestad, Theis

AU - Schau-Magnussen, Magnus

AU - Christensen, Jørn Bolstad

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N2 - 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. The Vilsmeier-Haack reaction (POCl 3/DMF) of 1,3,6,8-tetramethoxynaphthalene gave an unusual peri-cyclised dimer as well as the 1-naphthaldehyde. The dimer is a potent donor molecule.

AB - 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. The Vilsmeier-Haack reaction (POCl 3/DMF) of 1,3,6,8-tetramethoxynaphthalene gave an unusual peri-cyclised dimer as well as the 1-naphthaldehyde. The dimer is a potent donor molecule.

U2 - 10.1002/ejoc.201200512

DO - 10.1002/ejoc.201200512

M3 - Journal article

SN - 1434-193X

VL - 2012

SP - 4931

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JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 26

ER -

A peri-cyclised naphthalene dimer: synthesis and properties of an unusual vilsmeier-haack product of 1,3,6,8-tetramethoxynaphthalene

Abstract

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