Issue 7, 2013

Structural elucidation of homometallic anthracenolates synthesised via deprotonative metallation of anthrone

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

Supplementary files

Article information

Article type
Paper
Submitted
19 Sep 2012
Accepted
22 Nov 2012
First published
22 Nov 2012

Dalton Trans., 2013,42, 2512-2519

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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