Reactions of carbonyl compounds in basic solutions. Part 23.1 The mechanism of the base-catalysed ring fission of 2, 2-dihydroxyindane-1, 3-diones

K Bowden, S Rumpal

Index: Bowden, Keith; Rumpal, Sanjay Journal of the Chemical Society. Perkin Transactions 2, 1997 , # 5 p. 983 - 988

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Abstract

The base-catalysed ring fission of a series of substituted 2, 2-dihydroxyindane-1, 3-diones and phenalene-1, 3-dione has been studied in 30%(v/v) dioxane–water. The reaction proceeds in two distinct steps. The first is a relatively fast base-catalysed ring fission to give substituted o-carboxyphenylglyoxals, and the second is a rearrangement of the latter resulting in formation of substituted o-carboxymandelic acids. Rate coefficients for the ring ...