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Paper | Regular issue | Vol 75, No. 7, 2008, pp.1725-1734
Published online, 14th March, 2008
DOI: 10.3987/COM-08-11368
Synthesis of 5-(Adamantan-1-yl)-4,4-dimethyl-1-(3-oxyphenyl)-2,6,7-trioxabicyclo-[3.2.0]heptanes and Their Base-Induced Chemiluminescent Decomposition in Liquid/Solid Phase

Masakatsu Matsumoto,* Masatoshi Tanimura, Masahiko Tachi, and Nobuko Watanabe

*Department of Chemistry, Kanagawa University, Tsuchiya, Hiratsuka, Kanagawa 259-1293, Japan

Abstract

Singlet oxygenation of 4-(adamantan-1-yl)-5-(3-hydroxy)phenyl-1,2-dihydrofuran 4a effectively gave bicyclic dioxetane 3a as crystals with a high melting point. Dioxetane 3a decomposed rapidly accompanied by the emission of blue light, when treated with tetrabutylammonium fluoride (TBAF) in DMSO or acetonitrile. The chemiluminescence efficiency for 3a was as high as those for tert-butyl-analog 2. In addition to chemiluminescent decomposition in a liquid phase, a finely powdered mixture of crystalline 3a and crystalline dimethylaminopyridine (DMAP) emitted blue light upon heating at 80-110 °C while maintaining a solid state.