Though uncommon, stable free radicals are important probes for other organic and biochemical systems. The unpaired electron of a free radical can be detected directly through ESR, as well as exerting a local influence on nuclear spin relaxation times, and fluorescence lifetimes. Nitroxides have played a major role in such studies, but verdazyls are also interesting, particularly because they are stable common biological reductants (such as aspartic acid) and oxidants (such as hydrogen peroxide). Nevertheless introduction of a verdazyl requires a knowledge of what other chemical transformations can be accomplished in presence of a verdazyl. To investigate this area, we report the synthesis and properties of verdazyls with a variety of functional groups that can be useful for labelling purposes. These include carboxylic acids, amines and a chloromethyl group.

Reactions of 6-oxoverdazyls for use as spin probes

253rd National Meeting (2017)

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