Specific Photocyclization of 1,4-Diarylcyclohepta-1,3- dienes Having Naphthyl Group on 1- or 4-Position

Kenichi NAKABAYASHI,* Hironori ENAMI, Hideaki TSUKAMOTO and Akihiko OUCHI

Department of Chemistry, Faculty of Education and Culture, Miyazaki University; Gakuen-kibanadai-nishi 1-1, Miyazaki-shi 889-2192 Japan
National Institute of Materials and Chemical Research, AIST, MITI; 1-1 Higashi, Tsukuba-shi 305-8565 Japan

The direct photocyclization of four 1,4-diarylcyclohepta-1,3-dienes(1a--d) with different aryl groups (phenyl, 1-naphthyl, and 2-naphthyl groups) by a XeCl excimer laser (308 nm) in hexane gave 1,5-diarylbicyclo[3.2.0]hept-6-enes (2a--c). The efficiency of the photochemical cyclization and fluorescence quantum yield strongly depended upon the aromatic substituents and this is interpreted by the conformation of the molecules.

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