Rearrangement of Allyl Aryl Ethers; Part V: Reaction of 2,5-Dialkoxyhydroquinone with Cycloalkanediols

Benzo[1,4]dioxines 5 and 6 were prepared in a one pot reaction from 2,5-dialkoxy-hydroquinone 1 and cycloalkane-1,2-diol 2. Acid-catalyzed reaction of 1 and 2 yielded a mixture of cycloalkanobenzofuran 11 and spiro compound 12. The mechanisms of these novel reactions are also discussed.