Abstract: | Cycloheptacd]benzofurans 1a-c were synthesized by heating (5-oxo-5H-benzocyclohepten-4-yloxy)acetic acids 7a-c with sodium acetate in acetic anhydride or by irradiation of 7a-c in acetonitrile. Several reactions such as protonation, catalytic hydrogenation, Diels-Alder reaction, acylation, and photoreaction were examined for 1a-b . The results show that cycloheptacd]benzofurans have both properties of heptafulvene and benzofuran. The carbon-carbon double bond in the furan ring of 1a has aromatic character, however, the carbon-carbon double bonds in the seven-membered ring have olefinic character. |