- Concerning the efficient conversion of epoxy alcohols into epoxy ketones using dioxiranes
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Representative epoxy alcohols are cleanly converted into the corresponding epoxy ketones in high yield by selective oxidation using dimethyldioxirane (1a) and its trifluoro analogue (1b) under mild conditions. The oxidation is found to take place leaving the configuration at the epoxy functionality unaffected. The direct oxyfunctionalization of simple cyclic epoxides with the powerful dioxirane 1b provides another attractive method to access epoxy ketones regioselectively.
- D'Accolti, Lucia,Fusco, Caterina,Annese, Cosimo,Rella, Maria R.,Turteltaub, Joanna S.,Williard, Paul G.,Curci, Ruggero
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p. 8510 - 8513
(2007/10/03)
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- Heterolytic Oxygen-Oxygen Bond Formation via gem-Dialkylperoxonium Ions
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Different extents of decomposition for the cis and trans isomers of 4,5-epoxycyclo-octyl hydroperoxide coupled with the formation of oxygen (identified by Raman spectroscopy) and bicyclic ethers suggest a mechanism involving the heterolytic formation of protonated alkyl hydrotrioxides by nucleophilic attack of hydroperoxide on gem-dialkylperoxonium ions.
- Best, Stephen P.,Bloodworth, A. J.,Spencer, Michael D.
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p. 416 - 418
(2007/10/02)
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- Synthesis of 9-Oxabicyclonon-3-yne
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Starting with 1,5-cyclooctadiene (1), the title compound 9 is gained in a synthesis of seven steps. 9 exists in two conformations 9a and 9b, of which 9a shows a strong interaction between the oxygen atom and the strained triple bond.Thermal fragmentation of the 1,2,3-selenadiazole 7 is used for the introduction of the triple bond.The structural proof of 7 is performed by 2D-NMR spectroscopy.
- Meier, Herbert,Mayer, Winfried,Kolshorn, Heinz
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p. 685 - 690
(2007/10/02)
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