Iminyl radicals from alpha-azido o-iodoanilides via 1,5-H transfer reactions of aryl radicals: new transformation of alpha-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.
Bencivenni
Giorgio
G
Dipartimento di Chimica Organica A Mangini, Università di Bologna, Bologna, Italy.
Lanza
Tommaso
T
Leardini
Rino
R
Minozzi
Matteo
M
Nanni
Daniele
D
Spagnolo
Piero
P
Zanardi
Giuseppe
G