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Issue 7, 2013
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Structural elucidation of homometallic anthracenolates synthesised via deprotonative metallation of anthrone

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Abstract

Five novel neutral homometallic complexes which contain the anthracen-9-olate anion have been prepared and characterised by treating anthrone with an organometallic base to induce aromatisation. Three of these complexes [(donor)·M(OC14H9)]2 (2–4) are dimeric and contain sodium, lithium and potassium respectively. For 2 and 3 the donor is N,N,N′,N′-tetramethylethylenediamine (TMEDA) whilst for 4 it is N,N,N′,N′′,N′′-pentamethyldiethylenetriamine (PMDETA). When bimetallic reagents such as [(TMEDA)·Na(μ-tBu)(μ-TMP)Zn(tBu)] are employed, only the alkali-metal-containing species is isolated (e.g., 2 in this case). Providing a contrast, complexes 5 [(TMEDA)·Mg(OC14H9)nBu] and 6 [(TMEDA)·Zn(OC14H9)Et] are monomeric. The alkali metal complexes were prepared by reacting anthrone with one molar equivalent of either n-butylsodium, n-butyllithium or (trimethylsilyl)methylpotassium in the presence of the required donor solvent. For 5 and 6, equimolar quantities of di-n-butylmagnesium and diethylzinc, respectively, were reacted with anthrone in the presence of TMEDA. The solid-state structures and the arene solution structures of 2–6 have been determined by X-ray crystallography and NMR spectroscopy respectively.

Graphical abstract: Structural elucidation of homometallic anthracenolates synthesised via deprotonative metallation of anthrone

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Publication details

The article was received on 19 Sep 2012, accepted on 22 Nov 2012 and first published on 22 Nov 2012


Article type: Paper
DOI: 10.1039/C2DT32176A
Citation: Dalton Trans., 2013,42, 2512-2519
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    Structural elucidation of homometallic anthracenolates synthesised via deprotonative metallation of anthrone

    W. Clegg, B. J. Fleming, P. García-Álvarez, L. M. Hogg, A. R. Kennedy, J. Klett, A. J. Martínez-Martínez, R. E. Mulvey, L. Russo and C. T. O'Hara, Dalton Trans., 2013, 42, 2512
    DOI: 10.1039/C2DT32176A

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