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Short Paper | Regular issue | Vol 87, No. 6, 2013, pp.1319-1326
Published online, 30th April, 2013
DOI: 10.3987/COM-13-12718
Intramolecular [2π+2π]-Photocyclization and Conformational Preference of 5-(2-Benzo[b]thienyl)-5-ethoxy-5H-dibenzo[a,d]cycloheptene

Motoko Akita, Sin-ya Mohri, Mai Takahashi, and Keiji Kobayashi*

*Department of Chemistry, Faculty of Science, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japan

Abstract

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.