Cyclization of 3-cyclopent-2-enyl-4-hydroxy[1]benzopyran-2-one (1) with col
d cone. sulfuric acid gave a mixture of two products, 2 (10%) and 3 (80%).
However, on treatment with mercuric chloride 1 furnished the linear product
4 in 60% yield while with mercuric acetate the bicyclic product 8 was obta
ined in 50% yield. The structures of products are established by chemical c
orrelation.