Structural elucidation of homometallic anthracenolates synthesised via deprotonative metallation of anthroneElectronic supplementary information (ESI) available: X-ray data, NMR spectra. CCDC 892941-892945. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c2dt32176a

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(OC 14 H 9 )] 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- t Bu)(μ-TMP)Zn( t Bu)] are employed, only the alkali-metal-containing species is isolated ( e.g. , 2 in this case). Providing a contrast, complexes 5 [(TMEDA)·Mg(OC 14 H 9 ) n Bu] and 6 [(TMEDA)·Zn(OC 14 H 9 )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. Metallation of anthrone by Li, Na, K, Mg and Zn organometallics has produced the corresponding metal 9-anthracenolate complexes.