Photochemical Lumiketone-Type Rearrangement of 3-Methoxyphenol Promoted by AlBr3

Article abstract of DOI:10.1246/bcsj.64.3468

Irradition of 3-methoxyphenol in the presence of 2 equiv. of AlBr3 in CH2Cl2 gave 4-methoxybicyclo<3.1.0>hex-3-en-2-one in a 38percent yield. 3-Methoxy-2-methylphenol also yielded the lumiketone rearrangement product.On the other hand, 3-methoxy-4-methyl-, 3-methoxy-5-methyl-, and 5-methoxy-2-methylphenol underwent transposition of the methyl group to give equilibrium mixtures of the three methoxycresoles.