PUB - Publikationen an der Universität Bielefeld

The single functionalization of the parent centropolyindane hydrocarbons fenestrindane (2) and centrohexaindane (3) at the molecular arene periphery has been studied. The monoformylation of 2 and 3 using the Rieche method resulted in the corresponding aldehydes, 7 and 10, in 23% and 35% yield, respectively. The -Friedel-Crafts acetylation of 2 furnished 2-acetylfenestrindane (8) in 53% yield, and the Baeyer-Villiger oxidation of 7 followed by hydrolysis resulted in the 2-hydroxy-fenestrindane (9) in 72% yield. The results show that electrophilic attack at one of the eight or, respectively, even 12 equivalent positions of 2 and 3 is a viable method for the monofunctionalization of these polycyclic aromatic hydrocarbons.