Silver initiated rearrangement of N-chloroamines

Several secondary N-chloroamines were characterized by carbon-13 and proton NMR spectroscopy. The resulting chemical shifts were consistent with anticipated resonance and inductive effects exhibited by the compounds at hand. When allowed to stir for two days in the presence of silver tetrafluoroborate sealed under argon gas in the absence of light, two of the four N-chloroamines under investigation underwent rearrangement. The rearranged products were hydrolyzed upon work-up in a basic medium. The resulting anilines and elimination by-products were isolated by use of packed column chromatography. Separate syntheses of expected products were carried out to provide reference NMR spectra. Recovered compounds were also confirmed by mass spectroscopy and two dimensional NMR experiments.