| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1313493 | Journal of Fluorine Chemistry | 2016 | 5 Pages |
•Nitrosation of gem-bromofluorocyclopropanes is studied.•A nitrosyl chloride sulfur trioxide adduct is used as a reagent.•5-fluoro- and 5-bromoalkylisoxazoles were synthesized.•Fluorinated cyclopropanes exhibited excellent chemoselectivity for 5-fluoroisoxazoles.
A method for the synthesis of 5-fluoro- and 5-bromoalkylisoxazoles via nitrosation of alkylated gem-dihalocyclopropanes with a nitrosyl chloride sulfur trioxide adduct has been developed. In the case of bromofluorocyclopropanes the reaction proceeded with excellent chemoselectivity thus providing exclusively 5-fluoroisoxazoles.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideA method for the synthesis of 5-fluoro- and 5-bromoalkylisoxazoles via nitrosation of alkylated gem-dihalocyclopropanes with a nitrosyl chloride sulfur trioxide adduct has been developed. In the case of bromofluorocyclopropanes the reaction proceeded with excellent chemoselectivity thus providing exclusively 5-fluoroisoxazoles.
