The oxidative rearrangement of pentaalkoxychalcones using the hypervalent iodine compound, phenyliodine(III) bis(trifluoroacetate) (PIFA), has been examined. Treatment of 2,2′-bis(benzyloxy)-4′-methoxy-4,5-methylenedioxychalcone with PIFA gives a rearrangement product in low yield, but 2,2′-bis(benzyloxy)-3-bromo-4′-methoxy-4,5-methylenedioxychalcone yields the rearrangement product, which leads to (±)-bromopterocarpin and (±)-pterocarpin.
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Journal of the Chemical Society, Perkin Transactions 1
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