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Singlet-oxygenation of 3-hydroxyphenyl-substituted dihydrofurans fused with a cyclohexane 1a−c exclusively gave the corresponding syn/anti-stereoisomeric mixtures of dioxetanes 2a−c. The syn/anti-π-facial selectivity in the 1,2-cycloaddition of singlet oxygen (1O2) was found to be remarkably sensitive to the solvent as well as the reaction temperature. In fact, the solvent effect was so conspicuous...
Low-temperature singlet oxygenation of 1-alkoxy-1-aryl-2,2-diisopropylethylenes (9) gives the corresponding 1,2-dioxetanes (10) in high selectivity. Dioxetanes (10) are thermally stable enough to permit handling at room temperature, though an alkoxy group affects significantly their thermal stability and the order of half-life is MeO < EtO < i-PrO tert-BuO. On treatment with tetrabutylammonium...
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