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Issue 4, 2006
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Building an extended inverse crown motif via alkali-metal-mediated α-magnesiation of furan

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Abstract

The utility of inverse crown chemistry is extended to aromatic heterocycles, as furan is deprotonated selectively at the α-position by the mixed-metal alkyl-amido base [(TMEDA)·Na(Bun)(TMP)Mg(TMP)] to generate a transient intermediate which undergoes disproportionation to the disodium dimagnesium hexafuryl tri(thf) complex [{{(thf)3·Na2}{(TMEDA)·Mg2}(2-C4H3O)6}], a new type of inverse crown structure with triply-stabilized (through Mg–C σ, Na–O σ and Na⋯C–C π interactions) furyl ‘guest’ anions, and the tris(amide) [(TMEDA)x·NaMg(TMP)3].

Graphical abstract: Building an extended inverse crown motif via alkali-metal-mediated α-magnesiation of furan

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Article information


Submitted
24 Oct 2005
Accepted
08 Nov 2005
First published
02 Dec 2005

Chem. Commun., 2006, 417-419
Article type
Communication

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

D. V. Graham, E. Hevia, A. R. Kennedy, R. E. Mulvey, C. T. O'Hara and C. Talmard, Chem. Commun., 2006, 417
DOI: 10.1039/B514985A

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