Free-Radical Azidation with Gamma-N-15-labeled Phenylsulfonyl azide
Chemistry and Biochemistry
The gamma-nitrogen of phenylsulfonyl azide can be readily labeled with N-15 by treating benzenesulfonyl hydrazide with (NaNO2)-N-15. The resulting gamma-N-15-labeled sulfonyl azide reacts with carbon-centered free radicals to produce alkyl azides exclusively containing a C-N-15 bond. This chemistry provides valuable insight into the free-radical azidation mechanism as well as providing a mild method for the production of N-15-amines.
Masterson, D. S.,
(2007). Free-Radical Azidation with Gamma-N-15-labeled Phenylsulfonyl azide. Synlett(8), 1302-1304.
Available at: http://aquila.usm.edu/fac_pubs/9017