4-Fluoroanilines: synthesis and decomposition

Fourteen N- and/or 2-substituted 4-fluoroanilines were prepared (the series includes N–C2-bridged compounds). Some of them were found to be thermally unstable when dissolved in chloroform. Both 19F NMR spectra and comparison of GIAO-DFT calculated and experimental 13C chemical shifts were used to suggest decomposition products of 4-fluoroanilines.