Ring opening is preferred to dehydrogenation when 3,4-dihydrocoumarins react with ortho- or para-chloranil or with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) in alcoholic solvents, the quinones acting as Lewis acid catalysts. The alcoholysis products react further with DDQ to give coupled adducts.
S. M. Ali, J. W. A. Findlay and A. B. Turner, J. Chem. Soc., Perkin Trans. 1, 1976, 407 DOI: 10.1039/P19760000407
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