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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.
- Source :
-
Journal of Organic Chemistry . 6/20/2008, Vol. 73 Issue 12, p4721-4724. 4p. 1 Chart. - Publication Year :
- 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)alkyl radicals. The outcoming iminyls display a peculiar tendency to form corresponding nitriles by β-elimination of aminocarbonyl radicals. [ABSTRACT FROM AUTHOR]
- Subjects :
- *TRIBUTYLTIN
*HYDROGEN
*ACIDS
*RADICALS
*ELIMINATION (Mathematics)
*ARYL radicals
Subjects
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 73
- Issue :
- 12
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 32720171
- Full Text :
- https://doi.org/10.1021/jo800453z