A series of 10-membered cyclic 1, 5-diynes has been prepared with arene rings fused at positions C-3lC-4. The arenes include simple benzene rings, a naphthoquinone and naphthohydroquinone, and an anthraquinone and anthracene unit. Consistent with a simple picture relating the extent of double bond character in the ene part of the ene-diyne with the rate of arene-l, 4-diyl formation, the hydroquinone derivatives were much less reactive ...