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New reactivity and structural insights of alkali-metal-mediated alumination in directed ortho-alumination of a tertiary aromatic amide

Garcia-Alvarez, J. and Graham, D.V. and Kennedy, A.R. and Mulvey, R.E. and Weatherstone, S. (2006) New reactivity and structural insights of alkali-metal-mediated alumination in directed ortho-alumination of a tertiary aromatic amide. Chemical Communications (London) (30). pp. 3208-3210. ISSN 0009-241X

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Abstract

The first reported sodium alkyl(TMP)aluminate reagent to be synthesised and crystallographically characterised, [TMEDA·Na(µ-TMP)(µ-iBu)Al(iBu)2], reacts as an amido base towards phenylacetylene to form crystalline [(TMEDA)2·Na(µ-CCPh)(µ-iBu)Al(iBu)2]; whereas the congeneric TMEDA-stabilised lithium (TMP)aluminate exhibits dual alkyl/amido basicity in its reaction with N,N-diisopropylbenzamide to form a novel heterobimetallic-heterotrianionic crystalline complex [{PhC(O)N(iPr)2}·Li{2-[1-C(O)N(iPr)2]C6H4}{Me2NCH2CH2N(Me)CH2}Al(iBu)2], which, in addition to having an ortho-deprotonated benzamide ligand, also contains a methyl-deprotonated TMEDA ligand and a neutral benzamide molecule ligated to lithium.