Diels–Alder Additions to 2,2’‐Biaceanthrylene

Abstract A series of Diels–Alder reactions between the diene 2,2’‐biaceanthrylene and several dienophiles is presented. The diene is a cyclopenta‐fused polycyclic aromatic hydrocarbon with anthracene units linked by two cyclopentene rings. Depending on the dienophile, the major product was the result of a single addition (dimethyl acetylenedicarboxylate) or double addition (quinone, benzyne) to the diene. Single crystal X‐ray analysis of the quinone‐derivative shows a propeller‐like structure composed of mixed enantiomers. The synthesis and photophysical properties of these compounds are presented.