Synthesis of 3-vinyl-1,2,4-trioxolanes by a [3 + 2] cycloaddition of carbonyl oxides with .alpha.,.beta.-unsaturated carbonyl compounds
作者:Mitsuyuki Mori、Toshihiko Tabuchi、Masatomo Nojima、Shigekazu Kusabayashi
DOI:10.1021/jo00032a010
日期:1992.3
The [3 + 2] cycloaddition of a carbonyl oxide, generated by the ozonolysis of a vinyl ether, to an alpha,beta-unsaturated aldehyde gave the 3-vinyl-1,2,4-trioxolane (alpha-vinyl ozonide) in moderate yield. In contrast, alpha,beta-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.