Abstract
The Diels-Alder reactions between (E,E)-1,4-bis(4-bromophenyl)-1,3-butadiene and dienophiles and the use of the resulting adducts for macrocyclization and aromatization were established. Several functionalized macrocyclic structures bearing a functionalized [9]cycloparaphenylene or a higher homological unit were isolated. The distribution of the macrocyclic structures was found to be governed by the structures of the starting Diels-Alder adducts. An empirical correlation between the angles of the two 4-bromophenyl groups of the X-ray structures of the Diels-Alder adducts and the macrocyclization steps was observed.