Baker-Venkataraman Rearrangement

W. Baker, J. Chem. Soc. 1933, 1381; H. S. Mahal, K. Venkataraman, ibid. 1934, 1767.

Base-catalyzed rearrangement of o-acyloxyketones to β-diketones, important intermediates in the synthesis of chromones and flavones:



Gripenberg in The Chemistry of Flavonoid Compounds, Geissman, Ed. (New York, 1962) p 410. Mechanistic studies: K. Bowden, M. Chehel-Amiran, J. Chem. Soc. Perkin Trans. II 1986, 2039. Synthetic applications: P. K. Jain et al., Synthesis 1982, 221; J. Zhu et al., Chem. Commun. 1988, 1549; A. V. Kalinin et al., Tetrahedron Letters 39, 4995 (1998); D. C. G. Pinto et al., New J. Chem. 24, 85 (2000). Cf. Allan-Robinson Reaction; Kostanecki Acylation.