Abstract Novel reactions of 7, 7-dichloro-and 7, 7, 8-trichloro-3-oxo-2-oxabicyclo [4.2. 0] oct- 4-ene-6-carboxylates 5 with 1, 8-diazabicyclo [5.4. 0] undec-7-ene (DBU) in alcohol gave pyrano [4, 3-b] pyran-2, 5-diones 8 via (Z)-(2H-pyran-2-on-3-yl) butenoates 7. On the other hand, the same treatment of 7, 7, 8-trichloro-2-oxo-3-oxabicyclo-[4.2. 0] oct-4-ene-5- carboxylate 6b afforded 2-oxo-3-oxabicyclo [4.2. 0] oct-4, 7-diene-5-carboxylate 14 via ...