Synthesis and characterization of a novel N–F reagent derived from the ethano-Tröger's base: 1JFN coupling constants as a signature for the N–F bond

Abstract

Methylation of 2,8-dimethyl-6H,12H-5,11-ethanodibenzo[b,f][1,5]-diazocine (ethano-Tröger's base) with methyl iodide followed by ion metathesis and fluorination with N-fluoro-2,3,4,5,6-pentachloropyridinium triflate affords a new electrophilic N–F reagent, that is more reactive than Selectfluor. 2D ¹⁹F–¹⁵N HMQC experiments provide ¹J_NF coupling constants which are diagnostic for the N–F functional group.