Products from the reaction of pinosylvin 1a and pinosylvin dimethyl ether 1b with chlorine dioxide were characterized. Pinosylvin was more extensively degraded and gave benzoic acid, traces of other monomeric carboxylic acids, 2,6-dichloro- and 2,4,6-trichloropinosylvin 2, (n = 2 and 3), the benzilic acid rearrangement product 3 and the maleic acids 4a and 4b. Pinosylvin dimethyl ether gave similar monomeric products, the dichloroderivative 5, the dichloroepoxide 6 and a small amount of the dichlorohydroxyketone 7.
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