In attempts to make octaphenyldibenzofuran (7) and octaphenyldibenzothiophene (8), 2,5‐dibromofuran (4) 2,5‐dibromothiophene (5), respectively, were heated with tetracyclone (2) under forcing conditions, but only single addition products, such as 2‐bromo‐4,5,6,7‐tetraphenylbenzofuran (10) 2‐bromo‐4,5,6,7‐tetraphenylbenzothiophene (12) observed. However, when 2,5‐dibromothiophene‐1,1‐dioxide (6)...