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.
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.File in questo prodotto:
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