Some novel reactions of perfluoro-2,3-dialkyloxaziridines

Abstract

Perfluoro-2,3-dialkyloxaziridines rearrange at 120–160 °C into R₁NCF-OR′, quantitatively. Reaction with SbF₅ at elevated temperature leads to the formation of the isomeric alkoxy imines R_tONCFR′_f,. Reaction with CsF in the absence of a solvent results in formation of a mixture of the corresponding acyl fluoride R′_fC(O)F and N-fluoro imine R′_tCFNF. In contrast, reaction between perfluoro-2-butyl-3-propyloxaziridine and CsF in MeCN produces C₄F₉ONCFC₃F₇. Interaction of this oxaziridine with polyfluoro ketones and COF₂ in the presence of CsF in polar solvents leads to the formation of alkoxy imines R″_fONCFC₃F₇.