Jump to main content
Jump to site search

Issue 4, 2006
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 24 Oct 2005, accepted on 08 Nov 2005 and first published on 02 Dec 2005


Article type: Communication
DOI: 10.1039/B514985A
Citation: Chem. Commun., 2006, 417-419
  •   Request permissions

    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

Search articles by author