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- W2949103422 abstract "Cyclopropylidenecyclohexane undergoes the ene reaction with singlet oxygen. The migrating allylic hydrogen originates exclusively from the cyclohexane ring and therefore the hydroperoxy group becomes attached to the cyclopropane ring. Since the O - O bond in cyclopropyl peroxy systems is weak, the reaction product undergoes homolysis even at − 50°C and this also triggers rupture of the small ring.The resulting radical pair, consisting of 7 and the hydroxyl radical, recombines to form unsaturated β-hydroxy ketone 8 and the di-α, β-unsaturated ketone 9 (cf. Scheme 2).As a model for a cyclopropylidenecycloalkane containing no active allylic hydrogen, the adamantyl derivative 10 was subjected to photo-oxidation. In this case, the product is lactone 11 (yields in Table I), formed by early ring enlargement, i.e. before O - O rupture, as outlined in Scheme 4.The zwitter ion 15a isomerises to the key intermediate carbonyl oxide 17 and, as a result of the presence of the cyclobutane ring, this can rearrange to lactone 11 in various ways (cf. Scheme 5 and 6). By photo-oxygenation in 18O-labelled acetone, zwitter ion 17 is trapped by the solvent as an unstable ozonide which decomposes with formation of 18O-labelled lactone (Scheme 7). Photo-oxygenation in the presence of TCNE gives exclusively ketone 12 by deoxygenation of 17 (Scheme 4)." @default.
- W2949103422 created "2019-06-27" @default.
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- W2949103422 date "1985-09-24" @default.
- W2949103422 modified "2023-09-27" @default.
- W2949103422 title "ChemInform Abstract: THE CHEMISTRY OF SMALL-RING COMPOUNDS. PART 48. OXIDATION OF CYCLOPROPYLIDENECYCLOALKANES WITH SINGLET OXYGEN" @default.
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- W2949103422 doi "https://doi.org/10.1002/chin.198538122" @default.
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