The isomeric Diels-Alder adducts 3, obtained by cycloaddition of tetra
phenylcyclopentadienone to the ,5:12,13-bis(oxanorbornadieno)[2.2]para
cyclophanes syn,syn- and anti,-syn-2[], yield the unstable isobenzofu
ranophane 4 by consecutive extrusion of carbon monoxide and tetrapheny
lbenzene when heated to 180-degrees-C. The molecular ion of 4 was obse
rved in the EI mass spectrum. The stable tetraphenyl-substituted analo
gue 10 was synthesized independently from the previously unknown 4,5,1
2,13-tetrabenzoyl[2.2]paracyclophane (9). UV/Vis as well as fluorescen
ce spectra and an X-ray crystal structure analysis of 9 are reported.