Algar-Flynn-Oyamada Reaction

J. Algar, J. P. Flynn, Proc. Roy. Irish Acad. 42B, 1 (1934); B. Oyamada, J. Chem. Soc. Japan 55, 1256 (1934).

Alkaline hydrogen peroxide oxidation of o-hydroxyphenyl styryl ketones (chalcones) to flavonols via the intermediate dihydroflavonols:



T. S. Wheeler, Record Chem. Progr. 18, 133 (1957); W. P. Cullen et al., J. Chem. Soc. C 1971, 2848. Mechanism: T. R. Gormley, et al., Tetrahedron 29, 369 (1973); M. Bennett et al., ibid. 54, 9911 (1998). Synthetic applications: H. Wagner et al., ibid. 33, 1405 (1977); A. C. Jain et al., Bull. Chem. Soc. Japan 56, 1267 (1983). Cf. Auwers Synthesis.