1. 3-(Trihalometthyl)-3-alkoxy-1,2,4-trioxolanes
- Author
-
Sugiyama, Tomohito, Nojima, Masatomo, Krieger-Beck, Petra, Woo-Sun Kim, and Griesbaum, Karl
- Subjects
Ozone -- Methods ,Halocarbons -- Usage ,Carbonyl compounds -- Research ,Esters -- Research ,Biological sciences ,Chemistry - Abstract
A halo substituent in the alpha-position of esters enhances their reactivity towards carbonyl oxides. Taking a cue from the analogous dipolarophilicity of aldehydes and ketones, a series of vinyl ethers undergo ozonolysis in the presence of trifluoro- and trichloroacetates. Towards formaldehyde O-oxide, the esters yield more unsubstituted than halo-substituted (cross) ozonides. Towards alkyl- and arylcarbonyl oxides, the esters yield an abundance of cross-ozonides. These results contrast with the low cross-ozonide yield when ethyl acetate is used in place of trifluoroacetates.
- Published
- 1992