Building an extended inverse crown motif via alkali-metal-mediated α-magnesiation of furan
Literature Information
David V. Graham, Eva Hevia, Alan R. Kennedy, Robert E. Mulvey, Charles T. O'Hara, Christine Talmard
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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