A series of 10-membered cyclic 1, 5-diynes has been prepared with arene rings fused at
positions C-3/C-4. The arenes include simple benzene rings, a naphthoquinone and
naphthohydroquinone, and an anthraquinone and anthracene unit. Consistent with a simple
picture relating theextent of double bond character in the ene part of the ene-diyne with
therate of arene-l, 4-diyl formation, the hydroquinone derivatives were much less reactive
compared to the corresponding quiñones. Substituents such as propargylic hydroxyl or keto …

… A series of five arene and quinone derivatives with dialkynyl substituents in the ortho
positions and fixed in a 10-membered ring were prepared and tested with respect to thermal
rearrangement to the corresponding arene 1,4 diradicals. A series of cyclic o-dialkynylarenes
was prepared, including derivatives of benzene, 1,4-dimethoxynaphthalene, 9/10-dimethoxyanthracene,
and the corresponding quinones. The half-time for Bergman rearrangement in the presence
of … The arene analog, 4, is suggested to rearrange rapidly under the conditions of its …