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The oxidation of 1-trimethylsilyloxy,1-(2′-trimethylsilyloxyphenyl)ethene (6) with iodosobenzene, boron trifluoride etherate and water affords two major products, namely, 3-coumaranone (9, 31%) and 2, 2′-dihydroxyaceto-phenone (10, 25%). Formation of 9 is explained by neighboring group participation by the adjacent hydroxyl group.
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Moriarty et al. (1986) studied this question.
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