The radical reaction of tributyltin hydride with o-iodo-N-methylanilides derived from α-azido acids provides an excellent access to α-(aminocarbonyl)iminyl radicals through 1.5-hydrogen transfer reaction of initially formed aryl radicals followed by β-elimination of dinitrogen from ensuing α-azido-α-(aminocarbonyl)alkyls. The outcoming iminyl radicals display a peculiar tendency to form corresponding nitriles by β-elimination of aminocarbonyl radicals.
G. Bencivenni, T. Lanza, R. Leardini, M. Minozzi, D. Nanni, P. Spagnolo, et al. (2008). Iminyl Radicals from α-Azido o-Iodoanilides via 1,5-H Transfer Reaction of Aryl radicals: New Transformation of α-Azido Acids to Decarboxylated Nitriles. JOURNAL OF ORGANIC CHEMISTRY, 73, 4721-4724 [10.1021/jo800453z].
Iminyl Radicals from α-Azido o-Iodoanilides via 1,5-H Transfer Reaction of Aryl radicals: New Transformation of α-Azido Acids to Decarboxylated Nitriles.
BENCIVENNI, GIORGIO;LANZA, TOMMASO;LEARDINI, RINO;MINOZZI, MATTEO;NANNI, DANIELE;SPAGNOLO, PIERO;ZANARDI, GIUSEPPE
2008
Abstract
The radical reaction of tributyltin hydride with o-iodo-N-methylanilides derived from α-azido acids provides an excellent access to α-(aminocarbonyl)iminyl radicals through 1.5-hydrogen transfer reaction of initially formed aryl radicals followed by β-elimination of dinitrogen from ensuing α-azido-α-(aminocarbonyl)alkyls. The outcoming iminyl radicals display a peculiar tendency to form corresponding nitriles by β-elimination of aminocarbonyl radicals.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
