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.

Key words

azidation - free-radical chemistry - Nitrogen-15

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