Free-Radical Azidation with γ-¹⁵N-Labeled Phenylsulfonyl Azide

Abstract

The γ-nitrogen of phenylsulfonyl azide can be readily ­labeled with ¹⁵N by treating benzenesulfonyl hydrazide with Na¹⁵NO₂. The resulting γ-¹⁵N-labeled sulfonyl azide reacts with carbon-centered free radicals to produce alkyl azides exclusively containing a C-¹⁵N bond. This chemistry provides valuable insight into the free-radical azidation mechanism as well as providing a mild method for the production of ¹⁵N-amines.

azidation - free-radical chemistry - Nitrogen-15

References

1 Renaud P. Ollivier C. Panchaud P. Angew. Chem. Int. Ed.  2002,  41:  3460 

2 Ollivier C. Renaud P. J. Am. Chem. Soc.  2000,  122:  6496 

3 Ollivier C. Renaud P. J. Am. Chem. Soc.  2001,  123:  4714 

4 Ollivier C. Renaud P. Chem. Rev.  2001,  101:  3415 

5 Radicals in Organic Synthesis   Renaud P. Sibi MP. Wiley-VCH; New York: 2001. 

6 Panchaud P. Renaud P. J. Org. Chem.  2004,  69:  3205 

7 Panchaud P. Ollivier C. Renaud P. Zigmantas S. J. Org. Chem.  2004,  69:  2755 

8 Chabaud L. Landais Y. Renaud P. Org. Lett.  2002,  4:  4257 

9 Masterson DS. Porter NA. Org. Lett.  2002,  4:  4253 

10 Stefane B. Kocevar M. Polanc S. J. Org. Chem.  1997,  62:  7165 

11 Das S. Kumar SD. Thomas KG. Shivaramayya K. George MV. J. Org. Chem.  1994,  59:  628