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 |
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| Authors: | Bencivenni Giorgio Lanza Tommaso Leardini Rino Minozzi Matteo Nanni Daniele Spagnolo Piero Zanardi Giuseppe |
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| Affiliation: | Dipartimento di Chimica Organica A Mangini, Università di Bologna, Bologna, Italy. |
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| Abstract: | 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. |
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