The first isolation of α-hydroperoxy-N-arylimidoyl cyanides from 2-arylamino-2-alkenenitriles (α-cyanoenamines)

Treatment of N-1-(2-chloroalkylidene)arylamines 6 with KCN in CH3CN at reflux afforded 2-arylamino-2-alkenenitriles 3 (42–58%), which underwent autoxidation, yielding the corresponding α-hydroperoxyimidoyl cyanides (95–100%).