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- W2014394216 abstract "Cyclooctatetraene (1) reacted with photo-generated singlet oxygen to give the endoperoxide 7,8-dioxabicyclo[4.2.2]deca-2,4,9-triene (1a), which was further transformed to the cis-diepoxide 1b by catalytic rearrangement with Co-TTP to the unsaturated cis-diol 1c and the saturated cis-diol 1d by catalytic hydrogenation, to the saturated endoperoxide 1e by reaction with diimide, and to the epoxycyclooclatetraene If by deoxygenation with dimethylphosphine. Similarly, the methoxy-, phenyl- and methyl-substituted cyclooctatetraenes 3-5, respectively, gave the corresponding endoperoxides with the substituents located at the 1-position (3a, 5a), the 2-position (5b) and the 9-position (3b, 4a). Their structures were determined on the basis of their 1H- and 13C-NMR data and by means of chemical transformation to the corresponding syn-diepoxides, i.e. 5,10-dioxatricyclo[7.1.0.04,6]deca-2,7-dienes. The formation of the endoperoxides is postulated to involve an electron transfer mechanism to give the radical cation of cyclooctatetraene and the superoxide ion. The latter couples into the homotropylium-type zwitterionic intermediate and subsequent cyclization leads to the endoperoxides." @default.
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- W2014394216 date "1985-01-01" @default.
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- W2014394216 title "Synthesis of endoperoxides derived from cyclooctatetraenes via singlet oxygenation" @default.
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- W2014394216 doi "https://doi.org/10.1016/s0040-4020(01)96575-5" @default.
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