Journal of Organic Chemistry p. 1649 - 1652 (1992)
Update date:2022-08-04
Topics:
Mori, Mitsuyuki
Tabuchi, Toshihiko
Nojima, Masatomo
Kusabayashi, Shigekazu
The <3 + 2> 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.
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