Synthesis of 3-Vinyl-1,2,4-trioxolanes by a Cycloaddition of Carbonyl Oxides with α,β-Unsaturated Carbonyl Compounds

Article abstract of DOI:10.1021/jo00032a010

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.