Efficient synthesis of N-alkylformimidoyl cyanides

Article abstract of DOI:10.1016/S0040-4039(99)01608-1

N-Alkylformimidoyl cyanides (RRCHN=CHCN, 1) were obtained through a very efficient oxidation of N-alkylaminoacetonitriles (RRCHNHCH₂CN, 2) by aq. NaOCl. The reaction was run under very mild and simple conditions and afforded products (as E/Z isomer mixtures; E/Z ratio of 70-99%) in short reaction times (30-180 min), and in good to excellent yields (67-97%).