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

Literature Information

Publication Date 2005-12-02
DOI 10.1039/B514985A
Impact Factor 6.222
Authors

David V. Graham, Eva Hevia, Alan R. Kennedy, Robert E. Mulvey, Charles T. O'Hara, Christine Talmard


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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].

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