Preparation of an lsocyano-β-di ketone via its metal complexes, by use of metal ions as protecting groups

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A ligand containing isocyanlde and β-diketone functional groups, 3-(4-isocyanophenyl)-2,4-pentanedione (HacphNC), and several of its metal complexes have been prepared. The free isocyano-β-diketone could not be prepared by dehydration of the analogous formamide, HacphNHCHO, because of the reactivity of its β-diketone moiety. Instead, the metal complexes Al(acphNC) 3, Fe(acphNC) 3, Cu(acphNC) 2, and Zn(acphNC) 2 were synthesized by dehydration of the formamldo-β-diketonate complexes Al(acphNHCHO) 3, Fe(acphNHCHO) 3, Cu(acphNHCHO) 2, and Zn(acphNHCHO) 2. The free isocyano-β-diketone, HacphNC, can be liberated from its Al and Fe complexes by treatment with oxalate (C 2O 42-) and HC 2O 4-. In addition to these O-bound complexes, C(N)-bound complexes can be prepared by the reaction of either Al(acphNC) 3 or HacphNC with Au(I). X-ray analyses of HacphNC, Al(acphNC) 3, (HacphNC)AuCl, Cu(acphNHCHO) 2, trans-Zn(acphNHCHO) 2(H 2O) 2, and two other intermediates are also reported. © 2009 American Chemical Society.

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Inorganic Chemistry

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