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Structural elucidation of homometallic anthracenolates synthesised via deprotonative metallation of anthrone

Lookup NU author(s): Emeritus Professor Bill CleggORCiD


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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.

Publication metadata

Author(s): Clegg W, Fleming BJ, Garcia-Alvarez P, Hogg LM, Kennedy AR, Klett J, Martinez-Martinez AJ, Mulvey RE, Russo L, O'Hara CT

Publication type: Article

Publication status: Published

Journal: Dalton Transactions

Year: 2013

Volume: 42

Issue: 7

Pages: 2512-2519

Print publication date: 22/11/2012

ISSN (print): 1477-9226

ISSN (electronic): 1477-9234

Publisher: RSC Publications


DOI: 10.1039/c2dt32176a


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Funder referenceFunder name
FP7-2010-RG-268329European Union