Condensations of thiophene with ketones

Thiophene reacts with aliphatic ketones in aqueous 75% v/v sulfuric acid to give condensation products containing up to five thiophene units. Ketones bearing phenyl substituents yield mono- and di-styrylthiophenes. All the reactions occur at the C-2 and -5 positions of thiophene. 2,5-Bis(α-phenylstyryl)thiophene undergoes photocyclisation to give a dinaphthothiophene.