- Synthesis of 3-Vinyl-1,2,4-trioxolanes by a Cycloaddition of Carbonyl Oxides with α,β-Unsaturated Carbonyl Compounds
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The cycloaddition of a carbonyl oxide, generated by the ozonolysis of a vinyl ether, to an α,β-unsaturated aldehyde gave the 3-vinyl-1,2,4-trioxolane (α-vinyl ozonide) in moderate yield.In contrast, α,β-unsaturated ketones showed a very poor reactivity with carbonyl oxides.Benzylidenecyclohexanones were exceptions, from which the corresponding 3-vinyl-1,2,4-trioxolanes were obtained in excellent yields.Reaction of the 3-vinyl-1,2,4-trioxolanes with ozone led to the formation of the corresponding diozonides.
- Mori, Mitsuyuki,Tabuchi, Toshihiko,Nojima, Masatomo,Kusabayashi, Shigekazu
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p. 1649 - 1652
(2007/10/02)
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- Ozonolysis of Vinyl Ethers in the Presence of α-Diketones and α-Keto Esters
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Ozonolysis of vinyl ethers in the presence of α-diketones provided two types of products, i.e., a Baeyer-Villiger oxidation product and 3-acyl-1,2,4-trioxolane.The evidence suggests that the latter product is labile and, therefore, the former one might be produced by decomposition of the latter.In contrast, 1,2,4-trioxolane-3-carboxylates were stable.As a result, ozonolysis of vinyl ethers in the presence of α-keto esters yielded the expected ozonides in high yield.
- Tabuchi, Toshihiko,Nojima, Masatomo
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p. 6591 - 6595
(2007/10/02)
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