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Towards an understanding of the conjugate addition of organolithium reagents to α,β-unsaturated ketones: The isolation and solid-state structure of a monomeric lithium aluminate with very short agostic LiHC interactions1

Lookup NU author(s): Emeritus Professor Bill CleggORCiD, Dr Stephen Liddle


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Reaction of methylaluminium bis(2,6-di-tert-butyl-4-methylphenoxide) (MAD), 1, with alkyllithium reagents, R′Li (R′=Me, n-Bu or t-Bu), yields the solvent-dependent products lithium bis(2,6-di-tert-butyl-4-methylphenoxide)-THF complex, 2·THF, lithium dimethylbis(2,6-di-tert-butyl-4-methylphenoxide)aluminate, 3, a new type of lithium aluminate in which the lithium centre is stabilised by very short agostic LiH(t-Bu) interactions, and tris(alkyl)aluminium. The observation of these products suggests an explanation for the tendency of α,β-unsaturated ketones to undergo conjugate (rather than 1,2-) addition in the presence of MAD and organolithium reagents.

Publication metadata

Author(s): Clegg W, Lamb E, Liddle ST, Snaith R, Wheatley AEH

Publication type: Article

Publication status: Published

Journal: Journal of Organometallic Chemistry

Year: 1999

Volume: 573

Issue: 1-2

Pages: 305-312

Print publication date: 31/01/1999

ISSN (print): 0022-328X

ISSN (electronic): 1872-8561

Publisher: Elsevier


DOI: 10.1016/S0022-328X(98)00876-6


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