Synthetic Attempts towards [2.2]‐ and [2.3]Cyclopentadienophanes. The first [2.2]Cyclopentadienophane (=2,2,3,3,8,8,9,9‐octamethyltricyclo[8.2.1.14,7]tetradecatetraene; 1b) has been synthesized (Scheme 5) by reductive coupling of 6,6‐dimethylfulvene 3→5 (50%) followed by base‐induced twofold condensation of 1,2‐di(cyclopentadienyl)‐1,2‐dimethylbutane 5 with acetone to give difulvene 15 (95%). Reductive coupling of 15 gives a complex mixture of tautomers of 16, 17, and 1b, which contains ca. 50% of the target molecule 1b. Other synthetic attempts towards [2.2]cyclopentadienophanes 1a and 1b and [2.3]cyclopentadienophane 18 are discussed.