DOI: 10.1039/A606417E
(Paper)
Reference Section for: Chem. Commun., 1997, 741-742
Crystal and molecular structure of a ketocarboxylatocopper(ii) intermediate in the oxygenation of a copper(i) flavonolate complex
(Note: The full text of this document is currently only available in the PDF Version )
István Lippai, Gábor Speier, Gottfried Huttner and László Zsolnai
Abstract
Flavonol reacts with metallic copper in the presence of 2,2′-bipyridine to give dihydrogen and a mixture of compounds with the stoichiometric composition [CuI(bpy)(fla)] from which on standing only [CuI(bpy)2]2[CuI(fla)3 ] can be isolated; oxygenation of the solution of the mixture results in the ketocarboxylatocopper(II) complex [CuII(bpy)(fla)(2-HOC6H4COCO2 )], which hints at a copper-mediated oxidative cleavage of the pyranone ring in the flavonolate ligand via a 1,2-dioxethane intermediate by 3O2.
References
- D. W. Westlake, G. Talbot, E. R. Blakely and F. J. Simpson, Can. J. Microbiol., 1959, 5, 62; F. J. Simpson, G. Talbot and D. W. S. Westlake, Biochem. Biophys. Res. Commun., 1959, 2, 621; S. Hattori and I. Noguchi, Nature, 1959, 184, 1145 CAS; H. Sahamoto, Seikagu (J. Jpn. Biochem. Soc.), 1963, 35, 633 Search PubMed; T. Oka, F. J. Simpson and N. G. Krishnamurthy, Can. J. Microbiol., 1977, 16, 493.
- E. Makasheva and N. T. Golovkina, Zh. Obshch. Khim., 1973, 43, 1640; M. Thomson and C. R. Williams, Anal. Chim. Acta, 1976, 85, 375 CrossRef; K. Takamura and M. Ito, Chem. Pharm. Bull., 1977, 25, 3218 CAS.
- G. Speier, V. Fülöp and L. Párkányi, J. Chem. Soc., Chem. Commun., 1990, 512 RSC.
- É. Balogh-Hergovich, G. Speier and G. Argay, J. Chem. Soc., Chem. Commun., 1991, 551 RSC.
- M. Utaka, M. Hojo, Y. Fujii and A. Takeda, Chem. Lett., 1984, 635 CAS; M. Utaka and A. Takeda, J. Chem. Soc., Chem. Commun., 1985, 1824 RSC.
- T. Matsuura, Tetrahedron, 1977, 33, 2869 CrossRef CAS.
- I. Lippai, G. Speier, G. Huttner and L. Zsolnai, J. Chem. Soc., Dalton Trans., submitted Search PubMed.
- P. C. Arnaud, R. Faure and H. Loiseleur, Acta Crystallogr., Sect. C, 1986, 42, 814 CrossRef.
- G. M. Sheldrick, SHELXS-86, A Program for Crystal Structure Refinement, University of Göttingen, 1990; G. M. Sheldrick, SHELXL-93, A Program for Crystal Structure Refinement, University of Göttingen, 1993.