Structural elucidation of homometallic anthracenolates synthesised via deprotonative metallation of anthrone

Clegg, William and Fleming, Ben J. and Garcia-Alvarez, Pablo and Hogg, Lorna M. and Kennedy, Alan R. and Klett, Jan and Martinez-Martinez, Antonio J. and Mulvey, Robert E. and Russo, Luca and O'Hara, Charles T. (2013) Structural elucidation of homometallic anthracenolates synthesised via deprotonative metallation of anthrone. Dalton Transactions, 42 (7). pp. 2512-2519. ISSN 1477-9234

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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)center dot 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)center dot Na(mu-Bu-t)(mu-TMP)Zn(Bu-t)] are employed, only the alkali-metal-containing species is isolated (e.g., 2 in this case). Providing a contrast, complexes 5 [(TMEDA)center dot Mg(OC14H9)Bu-n] and 6 [(TMEDA)center dot 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.