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

Kemisk Institut

2 Citationer (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.

Originalsprog	Engelsk
Tidsskrift	European Journal of Organic Chemistry
Vol/bind	2012
Udgave nummer	26
Sider (fra-til)	4931-4936
Antal sider	6
ISSN	1434-193X
DOI	https://doi.org/10.1002/ejoc.201200512
Status	Udgivet - sep. 2012

Adgang til dokumentet

10.1002/ejoc.201200512

Citationsformater

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.
I: European Journal of Organic Chemistry, Bind 2012, Nr. 26, 09.2012, s. 4931-4936.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › peer review

@article{b45ebec4d99249279efa4e03b1b911e3,

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}",

year = "2012",

month = sep,

doi = "10.1002/ejoc.201200512",

language = "English",

volume = "2012",

pages = "4931--4936",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",

number = "26",

}

TY - JOUR

T1 - A peri-cyclised naphthalene dimer

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

PY - 2012/9

Y1 - 2012/9

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

EP - 4936

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

Adgang til dokumentet

Fingeraftryk

Citationsformater