4-ACETOXYTRICYCLO2,7>HEPT-4-EN-3-ONE; SYNTHESIS AND NOVEL BOND REORGANIZATION OF A VALENCE ISOMER OF 2-ACETOXYTROPONE

Article abstract of DOI:10.1016/S0040-4039(01)81878-5

4-Acetoxytricyclo<4.1.0.0^2,7>hept-4-en-3-one (3), a valence isomer of 2-acetoxytropone, was synthesized.Upon heating in pyridine at 150 deg C, 3 rearranged into 1-acetoxybicyclo<3.2.0>hepta-3,6-dien-2-one (9); the mechanism of which was examined by means of deuterium labeling experiments.