The reaction of 1,3-indandione with lead tetraacetate gave phthalic anhydride and 2,2-diacetoxy-1,3-indandione. The reaction of 2,2-dihydroxy-1,3-indandione gave phthalic anhydride. The reactions of 1,3(2H)-phenalenedione and 2,3-dihydroxy-1-phenalenone yielded acenaphthenequinone and 1,8-naphthalenedicarboxylic anhydride. The reactions of acenaphthenequinone and 2,2-dihydroxy-1,3-phenalenedione gave 1,8-naphthalenedicarboxylic anhydride with higher yields. The reactions of [2-14C]-labeled compounds showed that the middle carbon atom was lost.
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Ezoe et al. (1977) studied this question.
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