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The photoirradiation of 5-(2-benzo[b]thienyl)-5-ethoxy-5H-dibenzo[a.d]cycloheptene (2) in acetonitrile afforded a cagelike tetracyclic compound (1) via intramolecular [2π+2π]-photocycloaddition. The molecular and crystal structures of 1 and 2 were characterized by a single-crystal X-ray diffraction study. The formation of the cycloadduct is discussed in relation to the preferable conformation of the central C-C bond in 2, which was revealed to be in restricted rotation on the basis of the temperature-dependent 1H NMR spectra

Intramolecular [2π+2π]-Photocyclization and Conformational Preference of 5-(2-Benzo[b]thienyl)-5-ethoxy-5H-dibenzo[a,d]cycloheptene