Polyfluorinate arylnitrenes are useful reagents in organic synthesis, for the covalent modification of polymer surfaces and in photoaffinity labeling (PAL). This represents a new way to attach radiotracers to antibody fragments for diagnostic and therapeutic uses, in potential noninvasive imaging and therapy against cancer. The photochemical reactions of arylazides are presented. The desired reactions for PAL are insertion and addition since they result in covalent attachment. However, these particular reactions are not favored for the parent phenyl azide. In biochemistry, arylazides have been the most frequently used photoaffinity labels since they are relative easy to synthesize and to handle and because they are quite stable to physiological pH. Thus, a more complete understanding of photochemistry of a given arylazide is a basic requirement for its use in PAL. We will discuss the reactions and intermediates generated upon photolysis of fluorophenylazides and some examples of the application of these reagents in PAL and organic synthesis will be shown.

Photochemistry of arylazides

243rd National Meeting (2012)

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