Abstract
Oxidation of 2′-hydroxy-3′-nitrochalcones with thallium(III) nitrate gives (Z)-2-phenylmethylene-7-nitrobenzofuran-3(2H)-one derivatives, rather than the more usual 1,2-diaryl-3,3-dimethoxypropan-1-ones or the corresponding isoflavones.
Zusammenfassung
Die Oxidation von 2′-Hydroxy-3′-nitrochalconen mit Thallium(III)nitrat ergab (Z)-2-Phenylmethylen-7-nitro-3(2H)-benzofuranon-Derivate und nicht die üblichen 1,2-Diaryl-3,3-dimethoxypropan-1-one bzw. die entsprechenden Isoflavone.
References
McKillop A., Taylor E. C., Endeavour35, 88 (1976).
Taylor E. C., Conley R. A., Johnson D. K., McKillop A., Ford M. E., J. Org. Chem.45, 3433 (1980), and references therein.
Varma R. S., Chemistry and Industry (London)1982, 56.
Brady B. A., Kennedy J. A., O'Sullivan W. I., Tetrahedron29, 359 (1973).
Kurosawa K., Higuchi J., Bull. Chem. Soc. (Japan)45, 1132 (1972).
Hastings J. S.,Heller H. G., J. C. S. Perkin I1972, 2128.
King T. J.,Hastings J. S.,Heller H. G., J. C. S. Perkin I1975, 1455.
Seshadri S., Trivedi P. L., J. Org. Chem.25, 841 (1960).
Magnusson L. B., Postmus Jr.C., Craig C. A., J. Amer. Chem. Soc.85, 1711 (1963).
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Varma, R.S., Varma, M. Oxidative cyclisation of chalcones with thallium(III)nitrate: Synthesis of (Z)-2-phenylmethylene-7-nitro-3(2H)-benzofuranones. Monatsh Chem 113, 1469–1473 (1982). https://doi.org/10.1007/BF00808946
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DOI: https://doi.org/10.1007/BF00808946