Iminyl radicals from α-azido o-iodoanilides via 1,5-H transfer reactions of aryl radicals:: New transformation of α-azido acids to decarboxylated nitriles

The radical reaction of tributyltin hydride with o-iodo-N-methylanilides derived from alpha-azido acids provides an excellent access to alpha-(aminocarbonyl)iminyl radicals through 1,5-hydrogen transfer reaction of initially formed aryl radicals followed by beta-elimination of dinitrogen from ensuing alpha-azido-alpha-(aminocarbonyl)alkyl radicals. The outcoming iminyls display a peculiar tendency to form corresponding nitriles by beta-elimination of aminocarbonyl radicals.