Regioselective addition of bifunctional oximehydroxamic acid by the hydroxamic group to Pt(IV)-coordinated nitriles |
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Authors: | Konstantin V Luzyanin Markus Galanski Dmitry A Garnovskii |
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Institution: | a Centro de Química Estrutural, Complexo I, Instituto Superior Técnico, Av. Rovisco Pais, 1049-001 Lisbon, Portugal b Department of Chemistry, St. Petersburg State University, 198504 Stary Petergof, Russian Federation c Institute of Inorganic Chemistry - Bioinorganic, Environmental and Radiochemistry, University of Vienna, Währinger Str. 42, A-1090, Vienna, Austria |
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Abstract: | The metal-mediated coupling between the nitriles RCN in the platinum(IV) complexes trans-PtCl4(RCN)2] (R Me, Et, CH2Ph, Ph), cis/trans-PtCl4(MeCN)(Me2SO)] and the newly synthesized bifunctional oximehydroxamic acid, viz. N,2-dihydroxy-5-(1-hydroxyiminoethyl)benzamide, proceeds smoothly in CH2Cl2 at 40-45 °C to accomplish the new metallaligands HN C(R)ONHC( O)C6H3(2-OH)(5-C(Me) NOH) with pendant oxime functionalities due to the regioselective addition of the reagent via its hydroxamic groups. The obtained iminoligands exist in hydroxamic/hydroximic tautomeric equilibrium in solution. The structures of the isolated compounds are based on elemental analyses (C, H, N), IR, 1D 1H, 13C{1H}, and 2D NMR correlation experiments, i.e. 1H,13C-COSY, 1H,13C long range COSY, 1H,15N-COSY, and 1H,15N long range COSY. |
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Keywords: | Nitriles Platinum(IV) complexes Nucleophilic addition Oximehydroxamic acids Regioselectivity Imino complexes |
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