The McMurry coupling reaction of thiophene-derived dialdehydes has been employed as the key step in the synthesis of the sulfur-bridged annulenes 3, 4, 6-9, and 14. Dication 9 is the second example of a peripherally aromatic (26 n) dication of this class, while the 22 x annulene 14 is the first neutral aromatic annulene derived solely from thiophene.
