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Strathprints serves world leading Open Access research by the University of Strathclyde, including research by the Strathclyde Institute of Pharmacy and Biomedical Sciences (SIPBS), where research centres such as the Industrial Biotechnology Innovation Centre (IBioIC), the Cancer Research UK Formulation Unit, SeaBioTech and the Centre for Biophotonics are based.

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Building an extended inverse crown motif via alkali-metal-mediated alpha-magnesiation of furan

Graham, D.V. and Hevia, E. and Kennedy, A.R. and Mulvey, R.E. and O'Hara, C.T. and Talmard, C. (2006) Building an extended inverse crown motif via alkali-metal-mediated alpha-magnesiation of furan. Chemical Communications (London), 2006 (4). pp. 417-419. ISSN 0009-241X

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Abstract

The utility of inverse crown chemistry is extended to aromatic heterocycles, as furan is deprotonated selectively at the a-position by the mixed-metal alkyl-amido base [(TMEDA)Na-.(Bu-n)(TMP)Mg(TMP)] to generate a transient intermediate which undergoes disproportionation to the disodium dimagnesium hexafuryl tri(thf) complex [{{(thf)(3)Na-.(2)}{(TMEDA)Mg-.(2)}(2-C4H3O)(6)}(infinity)], a new type of inverse crown structure with triply-stabilized (through Mg-C sigma, Na-O sigma and (NaC)-C-...-C pi interactions) furyl 'guest' anions, and the tris(amide) [(TMEDA)(x)(NaMg)-Na-.(TMP)(3)].