N-fluoro-compounds. Part I. Synthesis of N-fluoro-compounds by direct fluorination of aqueous substrates

Abstract

The N-fluoro-compounds NF₂·CO·NH₂, MeNF·CO·NHMe, EtNF·CO·NHEt, NHF·CO₂Et, or MeNF₂ can be prepared by passing fluorine diluted with nitrogen through cold aqueous solutions of urea, NN′-dimethylurea, NN′-diethylurea (MeNF₂ and EtNF₂, respectively, are also obtained from the last two substrates), urethane, and trimethylurea, N-methylurethane, or N-methylacetamide, respectively; all these N-fluoro-compounds liberate iodine from aqueous potassium iodide and simultaneously lose their fluorine as fluoride ion. Possible fluorination mechanisms are discussed.