Facile Synthesis of Picene from 1,2-Di(1-naphthyl)ethane by 9-Fluorenone-Sensitized Photolysis
Organic Letters2011Vol. 13(10), pp. 2758–2761
Citations Over TimeTop 11% of 2011 papers
Hideki Okamoto, Minoru Yamaji, Shin Gohda, Yoshihiro Kubozono, Noriko Komura, Kaori Sato, Hisako Sugino, Kyosuke Satake
Abstract
A facile formation of picene was achieved by photosensitization of 1,2-di(1-naphthyl)ethane using 9-fluorenone as a sensitizer. This sensitized photoreaction is the first photochemical cyclization of ethylene-bridged naphthalene moieties to afford the picene skeleton. 5,8-Dibromopicene, prepared by this procedure using 1,2-di[1-(4-bromonaphthyl)]ethane as the substrate, was readily converted to novel functionalized picenes by conventional substitution and cross-coupling reactions.
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